[ CAS No. 500717-23-7 ] {[proInfo.proName]}

Name: 500717-23-7|Bis(9,9-dimethyl-9H-fluoren-2-yl)amine|97%
Brand: Ambeed
SKU: A267912
Price: 7.0 USD
Availability: InStock
Rating: 93 (28 reviews)

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

2D 3D

Structure of 500717-23-7 * Storage: {[proInfo.prStorage]}

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 110K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 500717-23-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 500717-23-7 ]

SDS Specification

Alternatived Products of [ 500717-23-7 ]

Product Details of [ 500717-23-7 ]

CAS No. :	500717-23-7	MDL No. :	MFCD23135317
Formula :	C₃₀H₂₇N	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LCSMGMWMTSWXDD-UHFFFAOYSA-N
M.W :	401.54	Pubchem ID :	59254080
Synonyms :

Calculated chemistry of [ 500717-23-7 ]

Physicochemical Properties

Num. heavy atoms :	31
Num. arom. heavy atoms :	24
Fraction Csp3 :	0.2
Num. rotatable bonds :	2
Num. H-bond acceptors :	0.0
Num. H-bond donors :	1.0
Molar Refractivity :	131.87
TPSA :	12.03 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-2.74 cm/s

Lipophilicity

Log Po/w (iLOGP) :	4.18
Log Po/w (XLOGP3) :	8.46
Log Po/w (WLOGP) :	8.04
Log Po/w (MLOGP) :	6.55
Log Po/w (SILICOS-IT) :	7.9
Consensus Log Po/w :	7.02

Druglikeness

Lipinski :	1.0
Ghose :	None
Veber :	0.0
Egan :	1.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-8.1
Solubility :	0.00000319 mg/ml ; 0.0000000079 mol/l
Class :	Poorly soluble
Log S (Ali) :	-8.58
Solubility :	0.00000105 mg/ml ; 0.0000000026 mol/l
Class :	Poorly soluble
Log S (SILICOS-IT) :	-11.99
Solubility :	0.0000000004 mg/ml ; 0.0 mol/l
Class :	Insoluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	3.41

Safety of [ 500717-23-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 500717-23-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 500717-23-7 ]
Downstream synthetic route of [ 500717-23-7 ]

[ 500717-23-7 ] Synthesis Path-Upstream 1~3

1
[ 1185882-60-3 ]
[ 500717-23-7 ]

Yield	Reaction Conditions	Operation in experiment
95%	Stage #1: With trifluoroacetic acid In tetrahydrofuran at 20℃; for 0.166667 h; Stage #2: With sodium hydroxide In tetrahydrofuran; dichloromethane; water	Bis(9,9-dimethyl-9H-fluoren-7-yl)amine (B) 0.4 g of tert-Butoxycarbonyl-protected arylamine 1 (0.8 mmol) was dissolved in 1 ml of tetrahydrofurane, and 8 ml of trifluoroacetic acid (TFA) was added to the resulting mixture. Then, the reaction mixture was stirred at room temperature for 10 minutes, thereby obtaining a solution having a color that turned dark green. TFA was evaporated in a vacuum, dichloromethane was added to the resultant, and the resultant was neutralized using an aqueous saturated sodium hydroxide solution. The mixture was extracted with solid dichloromethane solutions as described above, and the remaining moisture in the organic layer was removed. Then, column chromatography (stationary phase: silica gel, mobile phase: ethyl acetate:hexane=1:10 volume ratio) was performed on the resultant solution to obtain 0.3 g of pale yellow Compound 2 at a yield of 95percent. Mp: 178 °C ¹H NMR (300 MHz, (CD₃)₂CO):δ 7.7-7.67 (m, 4H), 7.48 (d, J=6.9 Hz), 7.36 (s, 2H), 7.31-7.22 (m, 4H), 7.18 (d, 2H J=7.2 Hz), 1.46 (s, 12H). ¹³C NMR(300MHz,(CD₃)₂CO):δ 155.97, 153.83, 144.45, 140.29, 132.48, 127.79, 126.73, 123.27, 121.67, 119.69, 117.32, 112.46, 47.28, 27.53.

Reference： [1] Tetrahedron, 2009, vol. 65, # 31, p. 6236 - 6243
[2] Patent: EP2371813, 2011, A1, . Location in patent: Page/Page column 13
[3] Patent: US2011/232763, 2011, A1,
[4] Organic Electronics: physics, materials, applications, 2014, vol. 15, # 11, p. 3316 - 3326

2
[ 108714-73-4 ]
[ 28320-31-2 ]
[ 500717-23-7 ]

Yield	Reaction Conditions	Operation in experiment
81%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tri-tert-butyl phosphine; sodium t-butanolate In toluene at 85℃; for 3 h;	6.27 g (30 mmol) of 2-amino-9,9'-dimethylfluorene, 5.46 g (20.0 mmol) of 2-bromo-9,9'-dimethylfluorene, 366 mg (0.4 mmol) of Pd₂(bda)₃ where dba is dibenzylideneacetone, 80 mg (0.4 mmol) of PtBu₃, and 2.88 g (30 mmol) of NaOtBu were dissolved in 60 mL of toluene, and the mixture was refluxed at 85°C for 3 hours. The mixture was cooled to room temperature and subjected to extraction three times with 50 mL of water and 50 mL of diethyl ether. An organic layer was collected and dried using magnesium sulfate to evaporate the solvent. The residue was separately purified using silica gel column chromatography to obtain 6.50 g of Intermediate I-1 (Yield: 81 percent) The produced compound was identified using 1H NMR and MS/FAB. C₃₀H₂₇N:calc. 401.21, found 402.231H NMR (400MHz, CDCl₃). δ7.78 (dd, 2H), 7.56 (d, 2H), 7.36-7.30 (m, 2H), 7.14-7.09 (m, 2H), 7.02 (d, 2H), 6.94 (d, 2H), 5.85 (s, 1H), 1.65 (s, 12H)
61%	With sodium t-butanolate In toluene at 90℃; for 3 h; Inert atmosphere	Synthesis Example 7: Synthesis of Compound 65; Synthesis of Intermediate 13 [Show Image] Under a nitrogen atmosphere, 1.91 g (7.0mmol) of 9,9'-dimethyl-2-bromofluorene, 2.2 g (10.5 mmol) of 9,9'-dimethyl-2-aminofluorene, 2.0 g (21 mmol) of t-BuONa, 130 mg (0.14mmol) of Pd₂(dba)₃, and 28 g (0.14mmol) of P(t-Bu)₃ were dissolved in 30 ml of toluene, and then the mixture was stirred at 90°C for 3 hours. After the reaction was completed, the reaction product was cooled to room temperature and extracted three times with distilled water and 50 ml of diethylether. The organic layer was collected and dried using magnesium sulfate to evaporate the solvent. The residue was separated and purified using silica gel column chromatography to obtain 1.7 g (yield: 61 percent) of Intermediate 13. This compound was identified using HR-MS. C₃₀H₂₇N calc.: 401.2143; found 401.2147.

Reference： [1] Patent: EP2581365, 2013, A1, . Location in patent: Paragraph 0129
[2] Patent: EP2292602, 2011, A1, . Location in patent: Page/Page column 31

3
[ 144981-85-1 ]
[ 500717-23-7 ]

Reference： [1] Tetrahedron, 2009, vol. 65, # 31, p. 6236 - 6243
[2] Patent: EP2371813, 2011, A1,
[3] Organic Electronics: physics, materials, applications, 2014, vol. 15, # 11, p. 3316 - 3326

[ 500717-23-7 ] Synthesis Path-Downstream 1~27

1
[ 869299-91-2 ]
[ 500717-23-7 ]
[ 1185882-61-4 ]

Yield	Reaction Conditions	Operation in experiment
50%	With tri-tert-butyl phosphine; palladium diacetate; caesium carbonate In toluene at 130℃; Inert atmosphere;
50%	With caesium carbonate In toluene at 130℃; Inert atmosphere;	1 7-(Bis(9,9-dimethyl-9H-fluoren-7-yl)amino)-9,9-spirobifluorene-2-carbaldehyde (2) 0.3 g of 2-bromo-7-formyl-9,9-spirobifluorene (A) (0.7 mmol), 0.44 g of Compound B (1.05 mmol), 0.023 g of palladium acetate (Pd(OAc)2) (0.1 mmol), 0.04 g of tertiarybutylphosphine (P(tBu)3) (0.2 mmol), and 1.4 g of cesium carbonate (Cs2CO3) (4.3 mmol) were dissolved in 15 ml of distilled toluene in a flask filled with nitrogen gas, and the mixture was refluxed at 130°C overnight. After the reaction was complete, the temperature of the flask was reduced to room temperature, and an aqueous saturated ammonium chloride solution was added to the resultant mixture. A dichloromethane layer was extracted, and the remaining moisture existing in the layer was removed with MgSO4. Then, column chromatography (stationary phase: silica gel, mobile phase: dichloromethane:hexane=3:1 volume ratio) was performed on the resultant to obtain 0.26 g of a desired Compound 2 at a yield of 50%. Mp: 180 °C 1HNMR(300MHz,(CD3)2CO):δ 9.85 (s, 1H), 8.12 (d, 1H. J=8.4Hz),8.03(d,1H,J=8.4Hz),7.97(d,1H,J=7.8Hz),7.86(d,2H,J=7.2Hz),7.7(d,2H,J=7.2Hz),7 .64(d,2H,J==8.1 Hz),7.45(d,2H,J=7.2Hz),7.35(m,12H),6.96(dd,2H,J=8.1 Hz),6.84(d,2H,J=7.5 Hz),6.56(s,1H),1.28(s,12H). 13CNMR(300MHz,(CD3)2CO):δ 191.91, 155.95, 154.39, 152.44, 150.41, 148.7, 148.53, 147.5, 142.55, 139.48, 136.41, 135.76, 135, 131.49, 129.01, 127.9, 127.66, 124.74, 124.65, 124.49, 123.41, 123.29, 121.75, 121.25, 120.74, 120.43, 119.99, 117.87, 66.52, 54.93, 47.42, 27.56.

2
[ 500717-23-7 ]
[ 1185882-63-6 ]
[ 1185882-64-7 ]

Yield	Reaction Conditions	Operation in experiment
50%	With tri-tert-butyl phosphine; palladium diacetate; caesium carbonate In toluene at 130℃; Inert atmosphere;
50%	Stage #1: N-(9,9-dimethyl-9H-fluoren- 2-yl)-9,9-dimethyl-9H-fluoren-2-amine; 4-(2-bromo-9,9-spirobifluoren-7-yl)benzaldehyde With caesium carbonate In toluene at 130℃; Stage #2: With ammonium chloride In water; toluene at 20℃;	2 4-(2-(Bis(9,9-dimethyl-9H-fluoren-7-yl)amino)-9,9-spirobifluoren-7-yl)benzaldehyde (7) 0.5 g of Compound B (1.25 mmol), 0.4 g of Compound C (0.8 mmol), 0.023 g of palladium acetate (Pd(OAc)2) (0.1 mmol), 0.04 g of t-butylphosphine (P(tBu)3) (0.2 mmol), and 1.4 g of cesium carbonate (Cs2CO3) (4.3 mmol) were dissolved in 15 ml of distilled toluene, and the mixture was refluxed at 130°C overnight. After the reaction was complete, the temperature of the flask was reduced to room temperature, and an aqueous saturated ammonium chloride solution was added to the resultant mixture. A dichloromethane layer was extracted, and the remaining moisture existing in the layer was removed with MgSO4. Then, column chromatography (stationary phase: silica gel, mobile phase: dichloromethane:hexane=3:1 volume ratio) was performed on the resultant to obtain 0.33 g of a desired Compound 7 at a yield of 50%. Mp:185°C. 1H NMR (300 MHz, CDCl3): δ 9.97 (s, 1H), 7.9 (m, 6H), 7.69 (m, 8H), 7.41 (m, 9H), 7.2 (m, 4H), 7.03 (m, 4H), 6.75 (s, 1H), 1.33 (s, 12H). 13C NMR (300 MHz, CDCl3):δ 191.85, 155.03, 153.6, 150.7, 149.96, 148.59, 148.41, 147.04, 142.26, 141.8, 138.97, 138.29, 135.42, 134.95, 134.35, 130.15, 128.03, 127.33, 127.07, 126.6, 124.29, 123.45, 122.7, 122.54, 121.05, 120.63, 120.29, 119.87, 119.5, 118.65, 66.09, 46.83, 27.13.

3
[ 1185882-60-3 ]
[ 500717-23-7 ]

Yield	Reaction Conditions	Operation in experiment
95%	With trifluoroacetic acid In tetrahydrofuran at 20℃; for 0.166667h; Inert atmosphere;
95%	Stage #1: tert-butyl bis(9,9-dimethyl-9H-fluoren-7-yl)carbamate With trifluoroacetic acid In tetrahydrofuran at 20℃; for 0.166667h; Stage #2: With sodium hydroxide In tetrahydrofuran; dichloromethane; water	1 Bis(9,9-dimethyl-9H-fluoren-7-yl)amine (B) 0.4 g of tert-Butoxycarbonyl-protected arylamine 1 (0.8 mmol) was dissolved in 1 ml of tetrahydrofurane, and 8 ml of trifluoroacetic acid (TFA) was added to the resulting mixture. Then, the reaction mixture was stirred at room temperature for 10 minutes, thereby obtaining a solution having a color that turned dark green. TFA was evaporated in a vacuum, dichloromethane was added to the resultant, and the resultant was neutralized using an aqueous saturated sodium hydroxide solution. The mixture was extracted with solid dichloromethane solutions as described above, and the remaining moisture in the organic layer was removed. Then, column chromatography (stationary phase: silica gel, mobile phase: ethyl acetate:hexane=1:10 volume ratio) was performed on the resultant solution to obtain 0.3 g of pale yellow Compound 2 at a yield of 95%. Mp: 178 °C 1H NMR (300 MHz, (CD3)2CO):δ 7.7-7.67 (m, 4H), 7.48 (d, J=6.9 Hz), 7.36 (s, 2H), 7.31-7.22 (m, 4H), 7.18 (d, 2H J=7.2 Hz), 1.46 (s, 12H). 13C NMR(300MHz,(CD3)2CO):δ 155.97, 153.83, 144.45, 140.29, 132.48, 127.79, 126.73, 123.27, 121.67, 119.69, 117.32, 112.46, 47.28, 27.53.
	With sodium hydroxide; trifluoroacetic acid In tetrahydrofuran; dichloromethane	S.1 Bis(9,9-dimethyl-9H-fluoren-7-yl)amine (B) Bis(9,9-dimethyl-9H-fluoren-7-yl)amine (B) 0.4 g of tert-Butoxycarbonyl-protected arylamine 1 (0.8 mmol) is dissolved in 1 ml of tetrahydrofurane, and 8 ml of trifluoroacetic acid (TFA) is added to the resulting mixture. Then, the reaction mixture is stirred at room temperature for 10 minutes, thereby obtaining a solution having a color that turns dark green. TFA is evaporated in a vacuum, dichloromethane is added to the resultant, and the resultant is neutralized using an aqueous saturated sodium hydroxide solution. The mixture is extracted with solid dichloromethane solutions as described above, and the remaining moisture in the organic layer is removed. Then, column chromatography (stationary phase:silica gel, mobile phase:ethyl acetate:hexane=1:10 volume ratio) is performed on the resultant solution to obtain 0.3 g of pale yellow Compound 2 at a yield of 95%. Mp: 178° C. 1H NMR (300 MHz, (CD3)2CO): δ 7.7-7.67 (m, 4H), 7.48 (d, J=6.9 Hz), 7.36 (s, 2H), 7.31-7.22 (m, 4H), 7.18 (d, 2H J=7.2 Hz), 1.46 (s, 12H). 13C NMR (300 MHz, (CD3)2CO): δ 155.97, 153.83, 144.45, 140.29, 132.48, 127.79, 126.73, 123.27, 121.67, 119.69, 117.32, 112.46, 47.28, 27.53.

With trifluoroacetic acid In tetrahydrofuran

Reference： [1]Location in patent: experimental part Cho, Nara; Choi, Hyunbong; Kim, Duckhyun; Song, Kihyung; Kang, Moon-sung; Kang, Sang Ook; Ko, Jaejung [Tetrahedron, 2009, vol. 65, # 31, p. 6236 - 6243]
[2]Current Patent Assignee: SAMSUNG SDI CO.,LTD. - EP2371813, 2011, A1 Location in patent: Page/Page column 13
[3]Current Patent Assignee: SAMSUNG SDI CO.,LTD. - US2011/232763, 2011, A1
[4]Choi, In Taek; You, Ban Seok; Eom, Yu Kyung; Ju, Myung Jong; Choi, Won Seok; Kang, Sung Ho; Kang, Min Soo; Seo, Kang Deuk; Hong, Ji Yeoun; Song, Sang Hyun; Yang, Ji-Woon; Kim, Hwan Kyu [Organic electronics, 2014, vol. 15, # 11, p. 3316 - 3326]

4
[ 500717-23-7 ]
[ 1185882-65-8 ]
[ 1185882-66-9 ]

Yield	Reaction Conditions	Operation in experiment
60%	With tri-tert-butyl phosphine; palladium diacetate; caesium carbonate In toluene at 130℃; Inert atmosphere;
60%	Stage #1: N-(9,9-dimethyl-9H-fluoren- 2-yl)-9,9-dimethyl-9H-fluoren-2-amine; 5-(2-bromo-9,9-spirobifluoren-7-yl)thiophene-2-carbaldehyde With caesium carbonate In toluene at 130℃; Stage #2: With ammonium chloride In water; toluene	3 5-(2-(Bis(9,9-dimethyl-9H-fluoren-7-yl)amino)-9,9-spirobifluoren-7-yl)thiophene-2-carbaldehyde (E) 1.05 g of Compound B (2.61 mmol), 0.88 g of Compound D (1.74 mmol), 0.016 g of palladium acetate (Pd(OAc)2) (0.071 mmol), 0.03 g of t-butylphosphine (P(tBu)3) (0.148 mmol), and 1.25 g of cesium carbonate (Cs2CO3) (3.84 mmol) were dissolved in 30 ml of distilled toluene, and the mixture was refluxed at 130°C overnight. After the reaction was complete, the temperature of the flask was reduced to room temperature, and an aqueous saturated ammonium chloride solution was added to the resultant mixture. The resultant mixture was extracted with chloroform and the remaining moisture existing in the layer was removed with MgSO4. Then, column chromatography (stationary phase: silica gel, mobile phase: dichloromethane:hexane=3:1 volume ratio) was performed on the resultant to obtain 1.15 g of a desired Compound E at a yield of 60%. Mp: 197°C. 1H NMR (300 MHz, CDCl3):δ 9.96 (s, 1H), 7.98 (m, 6H), 7.77 (dd, 3H), 7.68 (d, 2H, J= 7.5 Hz), 7.55(m, 8H), 7.31(dd ,6H), 7.11(m, 4H), 6,85(s, 1H), 1.46(s, 12H). 13C NMR (300 MHz, CDCl3): δ 182.69, 155.06, 154.64, 154.64, 150.74, 150.12, 148.28, 146.97, 143.22, 141.89, 141.8, 138.97, 137.35, 135.08, 134.46, 131.63, 128.07, 127.08, 126.64, 124.16, 124.01, 123.91, 123.55, 123.28, 122.57, 121.68, 121.14, 120.65, 120.36, 119.97, 119.52, 118.74, 118.47, 65.99, 46.86, 27.14.

5
[ 144981-85-1 ]
[ 500717-23-7 ]

Reference： [1]Tetrahedron,2009,vol. 65,p. 6236 - 6243
[2]Patent: EP2371813,2011,A1
[3]Organic electronics,2014,vol. 15,p. 3316 - 3326

6
[ 108714-73-4 ]
[ 28320-31-2 ]
[ 500717-23-7 ]

Yield	Reaction Conditions	Operation in experiment
84%	With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; XPhos; In toluene; at 105 - 110℃; for 2.5h;Inert atmosphere;	2-Bromo-9,9-dimethylhydrazine (12.0 g, 43.9 mmol),<strong>[108714-73-4]2-amino-9,9-dimethylhydrazine</strong> (10.1 g, 48.3 mmol),Tris(dibenzylideneacetone)dipalladium (0.4 g, 0.4 mmol),2-Dicyclohexylphosphino-2,4,6-triisopropylbiphenyl (0.4 g, 0.9 mmol) and sodium tert-butoxide (6.3 g, 65.9 mmol) were added to toluene (120 mL).Heat to 105-110 C under nitrogen, stir for 2.5 hours; cool to room temperature, wash the reaction twice with water, dry over magnesium sulfate, filter, pass the filtrate through a short silica gel column, remove the solvent under reduced pressure; use dichloromethane / ethanol The crude product was recrystallized and purified to give the crude solid intermediate VB (15.2 g, 84%).
81%	With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; at 85℃; for 3h;	6.27 g (30 mmol) of <strong>[108714-73-4]2-amino-9,9'-dimethylfluorene</strong>, 5.46 g (20.0 mmol) of 2-bromo-9,9'-dimethylfluorene, 366 mg (0.4 mmol) of Pd2(bda)3 where dba is dibenzylideneacetone, 80 mg (0.4 mmol) of PtBu3, and 2.88 g (30 mmol) of NaOtBu were dissolved in 60 mL of toluene, and the mixture was refluxed at 85C for 3 hours. The mixture was cooled to room temperature and subjected to extraction three times with 50 mL of water and 50 mL of diethyl ether. An organic layer was collected and dried using magnesium sulfate to evaporate the solvent. The residue was separately purified using silica gel column chromatography to obtain 6.50 g of Intermediate I-1 (Yield: 81 %) The produced compound was identified using 1H NMR and MS/FAB. C30H27N:calc. 401.21, found 402.231H NMR (400MHz, CDCl3). delta7.78 (dd, 2H), 7.56 (d, 2H), 7.36-7.30 (m, 2H), 7.14-7.09 (m, 2H), 7.02 (d, 2H), 6.94 (d, 2H), 5.85 (s, 1H), 1.65 (s, 12H)
61%	With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; In toluene; at 90℃; for 3h;Inert atmosphere;	Synthesis Example 7: Synthesis of Compound 65; Synthesis of Intermediate 13 [Show Image] Under a nitrogen atmosphere, 1.91 g (7.0mmol) of 9,9'-dimethyl-2-bromofluorene, 2.2 g (10.5 mmol) of 9,9'-dimethyl-2-aminofluorene, 2.0 g (21 mmol) of t-BuONa, 130 mg (0.14mmol) of Pd2(dba)3, and 28 g (0.14mmol) of P(t-Bu)3 were dissolved in 30 ml of toluene, and then the mixture was stirred at 90C for 3 hours. After the reaction was completed, the reaction product was cooled to room temperature and extracted three times with distilled water and 50 ml of diethylether. The organic layer was collected and dried using magnesium sulfate to evaporate the solvent. The residue was separated and purified using silica gel column chromatography to obtain 1.7 g (yield: 61 %) of Intermediate 13. This compound was identified using HR-MS. C30H27N calc.: 401.2143; found 401.2147.

60%	With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; tri tert-butylphosphoniumtetrafluoroborate; In toluene; at 90℃; for 19h;Inert atmosphere;	To a suspension of 22.6 g (82.7 mmol) of 2-bromo-9,9-dimethyl-9H-fluorene, 17.3 g (82.7 mmol) of <strong>[108714-73-4]9,9-dimethyl-9H-fluoren-2-amine</strong>, and 23. 8 g (248.1 mmol) of sodium ten-butanolate in 300 mL of of toluene were added 0.96 g (3.31 mmol) of tri-ten-butylphosphine tetrafluoroborate and 3.03 g (3.31 mmol) of Pd2(dba)3 under an argonatmosphere. The mixture was heated at 90C for 19 h. After cooling, 40 mL of saturated aqueous NH4CI solution were added. After 30 minutes, the combined phases were filtered through celite and extended with 500 mL of dichloromethane and 250 mL of water. The organic phase was separated and the aqueous phase was washed with 200 mL of dichloromethane. The combined organic phases were washed withsaturated NaCI solution, dried with MgSO4, and evaporated to dryness. The crude solid was crystallised from toluene to give the title compound as a white solid (20.0 g, 60%).
	With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; In toluene; at 110℃; for 24h;Inert atmosphere;	0.1 mol of raw material 2-amino-9,9-dimethylfluorene and 0.12 mol of raw material2-Bromo-9,9-dimethylphosphonium is dissolved in 500mL of anhydrous toluene. After deoxygenation, 0.005mol of Pd2 (dba) 3 and 0.15mol of tri-tert-butylphosphorus are added, and the reaction is performed at 110 C for 24 hours under an inert atmosphere.During the reaction, the progress of the reaction is continuously monitored by TLC. After the reaction of the raw materials is complete, cool,Filtration and rotary evaporation of the filtrate,The solvent was removed, and the crude product was passed through a silica gel column to obtain intermediate 1.

Reference： [1]Patent: CN110183332,2019,A .Location in patent: Paragraph 0107; 0108
[2]Patent: EP2581365,2013,A1 .Location in patent: Paragraph 0129
[3]Patent: EP2292602,2011,A1 .Location in patent: Page/Page column 31
[4]Patent: WO2018/206769,2018,A1 .Location in patent: Page/Page column 85; 86
[5]Patent: CN110317206,2019,A .Location in patent: Paragraph 0051-0053
[6]Patent: CN111233764,2020,A .Location in patent: Paragraph 0028; 0035

7
[ 27973-29-1 ]
[ 500717-23-7 ]
[ 1269014-11-0 ]

Yield	Reaction Conditions	Operation in experiment
63%	With sodium t-butanolate In toluene at 90℃; for 3h; Inert atmosphere;	7 Synthesis of Intermediate 14; [Show Image] Under a nitrogen atmosphere, 3.78 g (10.5 mmol) of 1,6-dibromopyrene, 2.8g (7.0 mmol) of Intermediate 13, 2.0 g (21 mmol) of t-BuONa, 130 mg (0.14 mmol) of Pd2(dba)3, and 28 mg (0.14 mmol) of P(t-Bu)3 were dissolved in 30 ml of toluene, and then the mixture was stirred at 90°C for 3 hours. After the reaction was completed, the reaction product was cooled to room temperature and extracted three times with distilled water and 50 ml of diethylether. The organic layer was collected and dried using magnesium sulfate to evaporate the solvent. The residue was separated and purified using silica gel column chromatography to obtain 3.0 g (yield: 63%) of Compound 14. This compound was identified using HR-MS. C46H34BrN calc.: 679.1875; found 679.1875.

Reference： [1]Current Patent Assignee: SAMSUNG ELECTRONICS CO.,LTD.; Samsung Display (in: Samsung) - EP2292602, 2011, A1 Location in patent: Page/Page column 31-32

8
[ 500717-23-7 ]
[ CAS Unavailable ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
40%	With palladium diacetate; sodium hydride; bis[2-(diphenylphosphino)phenyl] ether In tetrahydrofuran; mineral oil at 80℃; for 24h; Schlenk technique; Inert atmosphere;	1-4 1-4: Synthesis of 5-(4-bis(9,9-dimethyl-9H-fluoren-2-yl) amino)-10,15- diphenyl-20-(4-cyanophenyl) zinc porphyrin Sodium hydride (60%) (0.43 g, 10.62 mmol), palladium acetate (0.03 g, 0.14 mmol), bis (2-diphenylphosphino) ether (0.18 g, 0.34 mmol) and the compound 5,15-di-(phenyl)-10-(bromomethyl)-20-(4-benzonitrile) porphyrin zinc (0.5 g, 0.71 mmol), bis (9,9-dimethyl-9H-fluoren-2-yl) amine (1.8 g, 2.48mmol) were placed in 250 mL dried Schlenk flask, vacuumized and dried. After drying, tetrahydrofuran solvent 50 mL was added, refluxed under nitrogen at 80 ° C for 24 hours, followed by stirring. After the reaction was terminated, the temperature was cooled to room temperature, extracted with dichloromethane and the solvent was washed several times with distilled water. The organic layer was dried with MgSO4 and the solvent was removed under reduced pressure and separated by column chromatography (chloroform) to obtain the product. The yield was 40%.
28%	With palladium diacetate; sodium hydride; bis[2-(diphenylphosphino)phenyl] ether In tetrahydrofuran; mineral oil for 48h; Reflux;

Reference： [1]Current Patent Assignee: KOREA UNIVERSITY - KR101499476, 2015, B1 Location in patent: Paragraph 0104-0106
[2]Kang, Min Soo; Kang, Sung Ho; Kim, Sang Gyun; Choi, In Taek; Ryu, Jung Ho; Ju, Myung Jong; Cho, Daeheum; Lee, Jin Yong; Kim, Hwan Kyu [Chemical Communications, 2012, vol. 48, # 75, p. 9349 - 9351] Kang, Min Soo; Kang, Sung Ho; Kim, Sang Gyun; Choi, In Taek; Ryu, Jung Ho; Ju, Myung Jong; Kim, Hwan Kyu; Cho, Daeheum; Lee, Jin Yong [Chemical Communications, 2012, vol. 48, # 75, p. 9349 - 9351,3]

9
[ 500717-23-7 ]
[ 1350842-26-0 ]
[ 1350840-59-3 ]

Yield	Reaction Conditions	Operation in experiment
68%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tri-tert-butyl phosphine; sodium t-butanolate In toluene at 110℃; for 24h;	The intermediate D obtained from the above step, bis(9,9-dimethyl-9H-fluorene-2-yl)amine, Pd2(dba)3, P(tBu)3, and NaOtBu were dissolved in a toluene solvent, followed by reflux for 24 hours at 110° C. Upon completion of the reaction, the reaction product was subjected to vacuum filtration through Celite and silica gel by using a hot toluene solvent. The temperature of the filtrate was cooled to room temperature, and then the precipitated product was recrystallized again using toluene and acetone, with the result that desired compound 1-15 was obtained by a yield of 68%.
68%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tri-tert-butyl phosphine; sodium t-butanolate In toluene at 110℃; for 24h;	1 Synthesis of Compound 1-15 Intermediate D and the bis (9,9-dimethyl-9H-fluoren-2-yl) obtained in Step amine, Pd2 (dba) 3, P (tBu) 3 was dissolved and the solvent NaOtBu in toluene, 24 hours at 110 °C refluxed. After the reaction was completed the reaction was filtered under reduced pressure using a Celite (celite) and silica gel (silica-gel) using hot toluene (toluene) solvent. After cooling to room temperature, and then was re-crystallized using toluene and the precipitated product was again (toluene), and acetone (acetone) granulation to obtain the desired compound 1-15 in 68% yield.

Reference： [1]Current Patent Assignee: DUK SAN NEOLUX CO., LTD. - US2013/69049, 2013, A1 Location in patent: Paragraph 0057; 0067-0068
[2]Current Patent Assignee: DUKSAN HI METAL CO LTD - KR101604642, 2016, B1 Location in patent: Paragraph 0074-0077; 0086-0087

10
[ 500717-23-7 ]
[ 1257248-57-9 ]

Yield	Reaction Conditions	Operation in experiment
67%	With palladium diacetate; potassium carbonate In acetic acid at 110℃; for 24h;	1 Synthesis of Intermediate I-2 4.01 g (10.0 mmol) of Intermediate I-1, 1.12 g (0.5 mmol) of palladium (II) acetate (Pd(OAc)2), and 1.38 g (10.0 mmol) of K2CO3 were dissolved in 20 mL of acetic acid, and the mixture was refluxed at 110°C for 24 hours. The mixture was cooled to room temperature and subjected to extraction three times with 40 mL of water and 50 mL of diethyl ether. An organic layer was collected and dried using magnesium sulfate to evaporate the solvent. The residue was separately purified using silica gel column chromatography to obtain 68 g of Intermediate I-2 (Yield: 67 %) The produced compound was identified using 1H NMR and MS/FAB. C30H25N:calc. 399.20, found 400.191H NMR (400MHz, CDCl3) δ 8.58 (d, 2H), 8.12 (s, 1H), 7.96 (dd, 2H), 7.42 (s, 2H), 7.34-7.21 (m, 6H), 1.68 (s, 12H)

Reference： [1]Current Patent Assignee: Samsung Display (in: Samsung); SAMSUNG ELECTRONICS CO.,LTD. - EP2581365, 2013, A1 Location in patent: Paragraph 0130

11
[ 1074-24-4 ]
[ 500717-23-7 ]
[ 1838713-87-3 ]

Yield	Reaction Conditions	Operation in experiment
77%	With bis(dibenzylideneacetone)-palladium⁽⁰⁾; sodium t-butanolate In toluene at 95℃; for 4h;	2.1 Synthesis of intermediate 2-1 bis (9,9-dimethyl-9H-fluoren-2-yl) amine (4.0 g, 0.010 mol) 1,4-dibromo-2,5-dimethylbenzene in (2.6 g,0.010 mol), Pd (dba) 2 (0.5 g, 0.0005 mol), sodium-tert-butoxide (1.9 g, 100 mL to insert the Tol 0.020 mol ) 95 It was reacted by stirring for 4 hours at . After the reaction cooled to H20: After layer separation the MC column purification ( n - Hexane : MC ) toTo give the intermediate 2-1 4.5 g ( yield 77%). (M / z = 585)

Reference： [1]Current Patent Assignee: P&H TECH CO.,LTD. - KR2016/6007, 2016, A Location in patent: Paragraph 0178-0180

12
[ 319906-45-1 ]
[ 500717-23-7 ]
C₄₅H₃₈BrN [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With palladium diacetate; sodium t-butanolate; In toluene;Inert atmosphere; Reflux;	Compound I-43 (29.6 g, 73.8 mmol) was sequentially added to a round bottom flask.Compound II-43 (29.4 g, 73.8 mmol),t-BuONa (10.7 g, 111 mmol),Pd(OAc)2 (0.33 g, 1.47 mmol) and ultrasonically deoxygenated toluene (1.5 L),Reflux overnight under nitrogen,After the reaction solution was cooled, treated with ethyl acetate and water,The resulting organic layer was dried over MgSO 4 and the solvent was evaporated under reduced pressure.The crude compound III-43 was obtained.Silica gel as stationary phase, dichloromethane/hexane as eluent,Column chromatography of the crude product afforded compound III-43 (38.2 g, 77%).

Reference： [1]Patent: CN107652189,2018,A .Location in patent: Paragraph 0118; 0119-0121

13
[ 500717-23-7 ]
[ 2219355-67-4 ]
[ 2219355-44-7 ]

Yield	Reaction Conditions	Operation in experiment
65%	With palladium diacetate; sodium t-butanolate; XPhos In toluene at 110℃; Inert atmosphere;	1 Structure 9: In a 100 mL three-neck flask, Structure C1 (412 mg, 1.0 mmol, 412 g/mol) , bis (9, 9-dimethyl-9H-fluoren-2-yl) amine (442 mg, 1.1 mmol, 401.5 g/mol) , NaOBu-t (115 mg, 1.2 mmol, 96 g/mol) , X-Phos (24 mg, 5mmol, 476.7 g/mol) and Pd (OAc) 2 (11 mg, 5mmol, 224.5 g/mol) were added into Toluene (30 mL) , and the solution was stirred at 110 under N2 atmosphere overnight. After completion of the reaction, EtOAc (60 mL) was added, and the organic phase was washed with brine (2 × 150 mL) and dried over anhydrous Na2SO4. The solvent was removed by distillation under reduced pressure affording the crude products. The crude products were purified via silica gel column (eluent PE/DCM 10: 1-5: 1) , and then recrystalization in DCM/EtOH, DCM/PE, and EtOAc subsequently to give the final products as grey powders with a purity of 99.7as determined by HPLC and a yield of 65. 1H NMR (400 MHz, CDCl3, ppm) : 8.09-8.11 (d, J 8.0 Hz, 1H) , 7.91-7.93 (d, J 8.0 Hz, 1H) , 7.68-7.70 (d, J 8.8 Hz, 1H) , 7.60-7.66 (m, 5H) , 7.36-7.40 (m, 6H) , 7.28-7.35 (m, 8H) , 7.14-7.24 (m, 7H) , 3.84 (s, 3H) , 1.42 (s, 12H) . LC-MS-ESI (m/z) : calcd for C55H44N2: 732.35, found (M+H) +: 733.3585. The obtained Structure 9 has a HOMO level of -4.65 eV, a LUMO level of -0.90 eV, a triplet energy of 2.61 eV, and a hole mobility level of 0.22, as determined by the modeling method described above.

Reference： [1]Current Patent Assignee: DOW INC; DUPONT DE NEMOURS INC - WO2018/58497, 2018, A1 Location in patent: Page/Page column 17

14
[ 500717-23-7 ]
[ 1241891-64-4 ]
C₆₁H₄₆N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With bis(tri-t-butylphosphine)palladium⁽⁰⁾; sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene for 4h; Inert atmosphere; Reflux;	16 1) Synthesis of Compound (16) To a 500 ml round-bottomed flask under nitrogen was added compound B (7.0 g, 14.39 mmol), Bis (9,9-dimethyl-9H-fluoren-2-yl) amine (6.06 g, 15.11 mmol) was completely dissolved in 160 ml of xylene, sodium tert-butoxide (1.66 g, 17.27 mmol) was added, Bis (tri-tert-butylphosphine) palladium (0) (0.07 g, 0.14 mmol) was added thereto, followed by heating and stirring for 4 hours.After the temperature was lowered to room temperature and the salts were removed by filtration, the xylene was concentrated under reduced pressure and recrystallized from 210 ml of ethyl acetate to obtain Compound 30 (7.48 g, yield: 64%).

Reference： [1]Current Patent Assignee: LG CHEM CO.,LTD. - KR2018/27230, 2018, A Location in patent: Paragraph 0278-0282

15
[ 500717-23-7 ]
[ 1674334-59-8 ]
[ 2260615-57-2 ]

Yield	Reaction Conditions	Operation in experiment
69%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tri-tert-butyl phosphine; sodium t-butanolate In o-xylene; toluene for 2h; Reflux;	9 Example 9: Preparation of compound C-66 8 g of compound a-i (25 mmol), 9.9 g of compound b-9 (25 mmol), 1.13 g of tris(dibenzylideneaceton)dipalladium(0) (1.25 mmol), 1 mL of tri-tert-butylphosphine (2.5 mmol, 50% o-xylene solution), 5.9 g of sodium tert-butoxide (62 mmol), and 125 mL of toluene were introduced into a reaction vessel, and the mixture was refluxed for 2 hours. The reaction solution was cooled to room temperature, and the solvent was then removed by a rotary evaporator. The residue was purified by column chromatography to obtain 11 g of compound C-66 (yield: 69%).

Reference： [1]Current Patent Assignee: DUPONT DE NEMOURS INC - WO2019/4587, 2019, A1 Location in patent: Paragraph 172; 173; 174

16
[ 106-37-6 ]
[ 500717-23-7 ]
[ 313050-71-4 ]

Yield	Reaction Conditions	Operation in experiment
75.5%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; triphenylphosphine; sodium t-butanolate In toluene at 95℃; for 24h; Inert atmosphere;	1 Take intermediate I-1 as an example: Weigh 0.02mol of reactant II-1 and 0.03mol of reactant III-1,Dissolve in toluene; add 0.0002mol Pd2 (dba) 3, 0.0004mol P (Ph) 3, 0.09mol sodium tert-butoxide; in an inert atmosphere, react the mixed solution of the above reactants at 95C for 24 hoursIt was naturally cooled to room temperature, filtered, and the filtrate was spin-evaporated to no fractions and passed through a neutral silica gel column to obtain the target product intermediate I-1; HPLC purity 99.53%, yield 75.5%; HRMS (EI) (high resolution mass spectrometry): theory The value is 555.1562, and the measured value is 555.1578.
	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tri-tert-butyl phosphine In toluene at 110℃; for 24h; Inert atmosphere;	2 Synthesis example 2 (synthesis of intermediate 2) Dissolve 0.02 mol of Intermediate 1 and 0.024 mol of 1,4-dibromobenzene in 300 mL of anhydrous toluene, add 0.001 mol of Pd2 (dba) 3 and 0.03 mol of tri-tert-butyl phosphorus after deoxygenation,Reaction at 110 ° C for 24 hours under an inert atmosphere,During the reaction, the progress of the reaction is continuously monitored by TLC. After the reaction of the raw materials is complete, cool,Filtration, rotary evaporation of the filtrate to remove the solvent, the crude product was passed through a silica gel column,To obtain intermediate 2;
	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; triphenylphosphine; sodium t-butanolate In toluene at 105℃; for 24h; Inert atmosphere;	2 In a 250 ml three-necked flask, under the protection of nitrogen, add 0.01 mol of intermediate B2, 0.012 mol of raw material N1, 150 ml of toluene and mix, then add 5 × 10-5 mol Pd2(dba)3, 5 × 10-5mol P(Ph)3, 0.03mol sodium tert-butoxide, heated to 105 °C, and reacted at reflux for 24 hours. Sampling points showed no bromide remaining and the reaction was complete;It was naturally cooled to room temperature, filtered, and the filtrate was spin-evaporated to no fractions and passed through a neutral silica gel column to obtain the target product intermediate C1

61.9 %

With palladium diacetate; caesium carbonate; Xantphos In toluene at 70℃;

8.1 (1) Preparation Example 1: Synthesis of Intermediate 346-1 1,4-Dibromobenzene (10.0 g, 0.042 mol), Bis(9,9-dimethyl-9H-fluoren-2-yl)amine (25.5 g, 0.063 mol), Cs2CO3 (41.4 g, 0.126 mol), Pd(OAC ) 2 (0.4 g, 1.68 mmol) and Xant-phos (2.0 g, 3.36 mmol) were added with 150 mL of Toluene and reacted by stirring at 70 °C for 4 hours.After completion of the reaction, the mixture was extracted, concentrated, and then columnized to obtain 14.6 g of intermediate 346-1 (yield: 61.9%).

Reference： [1]Current Patent Assignee: VALIANT CO., LTD. - CN110526825, 2019, A Location in patent: Paragraph 0061-0066
[2]Current Patent Assignee: VALIANT CO., LTD. - CN110317206, 2019, A Location in patent: Paragraph 0054-0056
[3]Current Patent Assignee: VALIANT CO., LTD. - CN110343049, 2019, A Location in patent: Paragraph 0079; 0084; 0085
[4]Current Patent Assignee: P&H TECH CO.,LTD. - KR2023/56130, 2023, A Location in patent: Paragraph 0261-0264

17
[ 500717-23-7 ]
[ 2417805-31-1 ]
[ 2417805-38-8 ]

Yield	Reaction Conditions	Operation in experiment
75.3%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tri-tert-butyl phosphine; sodium t-butanolate In toluene at 105℃; for 24h; Inert atmosphere;	3 Example 3: Synthesis of Compound 3: In a 250 ml three-necked flask, add 0.01 mol of reactant I-1, 0.012 mol of reactant II-1, and 150 ml of toluene while mixing under nitrogen.Then add 5 X 10-5mol Pd2(dba)3, 5 X 10-5mol P(t-Bu)3 0.03mol sodium tert-butoxide, heat to 105 °C, and react at reflux for 24 hours. Sampling plate showed no bromide remaining and the reaction was complete; naturally cooled to room temperature, filtered, and the filtrate was spin-evaporated to no fractions, passed through a neutral silica gel column to obtain the target product,The purity of HPLC was 99.76%, and the yield was 75.3%.HRMS (EI): The molecular weight of the material is 743.3552, and the measured molecular weight is 743.3549.

Reference： [1]Current Patent Assignee: VALIANT CO., LTD. - CN110526825, 2019, A Location in patent: Paragraph 0076-0078

18
[ 500717-23-7 ]
[ 2376733-15-0 ]
[ 2379778-46-6 ]

Yield	Reaction Conditions	Operation in experiment
81%	With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾; sodium t-butanolate In toluene for 4h; Reflux;	1 Example 1: Synthesis of Compound 3 In a nitrogen atmosphere, 0.005 mol of the prepared intermediate C-1,0.006 mol of raw material D, 0.01 mol of sodium tert-butoxide, 3 × 10-4 mol of Pd (dba) 2, and 1.2 × 10-3 mol of tri-tert-butyl phosphorus,Then, 60 ml of toluene was added to dissolve it, heated to reflux, and reacted for 4 hours. The reaction was observed by TLC until the reaction was completed.It was left to cool to room temperature, water was added to the reaction system for extraction, and the liquid phase was separated. The organic phase was subjected to rotary evaporation under reduced pressure until no fractions were obtained.The obtained material was purified through a silica gel column to obtain the titled target product, with a purity of 99.7% and a yield of 81 %

Reference： [1]Current Patent Assignee: VALIANT CO., LTD. - CN110577510, 2019, A Location in patent: Paragraph 0121-0125

19
[ 500717-23-7 ]
[ 2247486-94-6 ]
[ 2247486-95-7 ]

Yield	Reaction Conditions	Operation in experiment
80%	Stage #1: N-(9,9-dimethyl-9H-fluoren- 2-yl)-9,9-dimethyl-9H-fluoren-2-amine; C₄₀H₄₄Br₂S₂ With palladium diacetate; sodium t-butanolate In toluene at 85℃; Inert atmosphere; Stage #2: With tri-tert-butyl phosphine In toluene for 12h; Inert atmosphere;	1 Example 1 Preparation of Compound B1 Under an argon atmosphere,In a 100mL three-necked flask, add 2,9-dibromo-7,7,14,14-tetrabutyl-7,14-dihydroperylene[1,2-b:7,8-b']dithiophene (1.80g, 2.4mol),Bis(9,9-dimethyl-9H-fluoren-2-yl)amine (2.02g, 5.0mmol), sodium tert-butyl alkoxide (1.84g, 19.2mmol),Palladium acetate (27mg, 0.12mmol) and 50ml toluene. Heat and stir to 85 , add 0.12ml tri-tert-butylphosphine toluene solution (0.24mmol, 2mol/L),Reaction 12h.After stopping the reaction, the solvent was concentrated, and the crude product was purified by column chromatography. A mixed solvent of petroleum ether and dichloromethane (2/1, v/v) was used as the eluent. The green solid was finally obtained and named compound B1.

Reference： [1]Current Patent Assignee: SOUTH CHINA UNIVERSITY OF TECHNOLOGY - CN108359443, 2020, B Location in patent: Paragraph 0072-0077

20
[ 500717-23-7 ]
[ 2541061-24-7 ]
[ 2541058-86-8 ]

Yield	Reaction Conditions	Operation in experiment
78.4%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tri-tert-butyl phosphine; sodium t-butanolate In toluene at 100℃; for 24h; Inert atmosphere;	4 Example 4 Preparation of compound 49 In a nitrogen atmosphere, 0.01 mol of intermediate I-4, 0.015 mol of raw material IV-4, 0.03 mol of sodium tert-butoxide,5×10-5mol Pd2(dba)3 and 5×10-5mol tri-tert-butylphosphine,then add 150ml of toluene to dissolve it, heat to 100°C, reflux for 24 hours, Use TLC to observe the reaction until the reaction is complete.Naturally cool to room temperature, filter, and spin-evaporate the filtrate to no fraction.The obtained material was purified by a silica gel column (petroleum ether as the eluent) to obtain the target product with a purity of 99.8% and a yield of 78.4%.

Reference： [1]Current Patent Assignee: VALIANT CO., LTD. - CN111362810, 2020, A Location in patent: Paragraph 0124-0126

21
[ 500717-23-7 ]
[ 2097124-40-6 ]
[ 2252483-17-1 ]

Yield	Reaction Conditions	Operation in experiment
58.5%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tri-tert-butyl phosphine; sodium t-butanolate In toluene for 5h; Inert atmosphere; Reflux;	15 Under nitrogen protection, compound 15-a (0.8g, 437.37g/mol, 1.83mmol), compound 15-b (1.1eq, 0.81g, 401.54g/mol, 2.01mmol), sodium tert-butoxide (1.1eq, 0.19g, 96.1g/mol, 2.02mmol), tris(dibenzylideneacetone) dipalladium (0.05eq, 0.084g, 915g/mol, 0.092mmol), tri-tert-butylphosphine (0.05eq, 0.019g, 202.32 g/mol, 0.092mol) and toluene (16ml) were added to the reaction flask. After the addition, the temperature was raised to reflux and reacted for 5h. After the reaction was completed, the temperature was lowered to room temperature and 16ml of water was added and stirred for 15min. The filtrate was filtered, and the filtrate was filtered through diatomaceous earth. After liquid separation, the organic phase was obtained. The organic phase was dried with anhydrous magnesium sulfate and spin-dried. After purification by column chromatography, the hole transport material (193) (0.81g, yield 58.5%) was obtained.

Reference： [1]Current Patent Assignee: NANJING TOPTO SEMICONDUCTOR MATERIAL CO LTD - CN112745229, 2021, A Location in patent: Paragraph 0159-0163

22
[ 500717-23-7 ]
[ CAS Unavailable ]
[ 2648595-38-2 ]

Yield	Reaction Conditions	Operation in experiment
76%	With tri-tert-butyl phosphine; palladium diacetate; caesium carbonate In toluene at 80℃; for 18h; Inert atmosphere;	7 Preparation of compound 7: Under nitrogen atmosphere, weigh out tris(2,4,6-trichlorophenyl)methyl radical (830mg, 1.5mmol), bis(9,9-dimethyl-9H-fluoren-2-yl)amine (402mg, 1.0mmol), Pd(OAc)2(74mg, 0.33mmol), P(t-Bu)3(2.0g, 10wt% toluene solution, 0.99mmol) and Cs2CO3(1.47g, 4.5mmol), dissolved in 20mL of toluene, heated to 80°C, and reacted for 18 hours.After the reaction, the toluene in the reaction system was removed, and the crude product was separated and purified by silica gel column chromatography to obtain 698 mg of compound 7 with a yield of 76%. The mass spectrum is shown in FIG. 3.Since free radicals have no nuclear magnetic signal, they are characterized by high-resolution mass spectrometry. The product HRMS (ESI, m/z): calculated value, 917.9984; measured value, 917.9976.

Reference： [1]Current Patent Assignee: FUDAN UNIVERSITY - CN112876368, 2021, A Location in patent: Paragraph 0068-0071

23
[ 589-87-7 ]
[ 500717-23-7 ]
[ 313050-71-4 ]

Yield	Reaction Conditions	Operation in experiment
82%	With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; 1,1'-bis(diphenylphosphanyl)ferrocene; sodium tertiary butoxide In toluene at 90℃; for 24h; Inert atmosphere;	Synthesis of N-(4-bromophenyl)-N-(4-methoxyphenyl)-9,9-dimethyl-9H-fluoren-2-amine (5): General procedure: A mixture of 4 (4.10 g, 13 mmol), 4-bromoiodobenzene (4.62 g, 16.40 mmol), tBuONa (1.89 g, 19.70 mmol),Pd2(dba)3CHCl3 (0.07 g, 0.07 mmol) and dppf (1, 10-bis(diphenylphosphino)ferrocene) (0.06 g, 0.10 mmol) was heated in toluene (30 mL),under a nitrogen atmosphere, at 90 C for 24 h. After cooling down the reaction to room temperature, extracted three times with water (20 mL)and ethyl acetate (40 mL). The organic layer was collected and evaporatedunder reduced pressure. The product was purified by columnchromatography (petroleum ether/dichloromethane = 3:1 vol/vol) andcollected as off-white solid in 85% yield.

Reference： [1]Chen, Cheng; Cheng, Ming; Ding, Xingdong; Miao, Yawei; Wang, Haoxin; Wang, Linqin; Zhai, Mengde [Dyes and Pigments, 2022, vol. 202]

24
[ 500717-23-7 ]
[ 2796254-92-5 ]
[ 2796254-57-2 ]

Yield	Reaction Conditions	Operation in experiment
82%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tri-tert-butyl phosphine; sodium tertiary butoxide In toluene at 115℃; for 7h; Inert atmosphere;	3.3 Step 3: Under the protection of N2, intermediate D-298 (34 mmol) and reactant E-298 (40.8 mmol) were added to the reaction vessel after dissolving in toluene, Pd2(dba)3 (0.34 mmol), P(t-Bu)3 (1.7 mmol), t-BuONa (68 mmol); after adding, the temperature was raised to 115 ° C, and the reaction was carried out for 7 h; using diatomaceous earth to filter while hot to remove salt and catalyst, after the filtrate was cooled to room temperature, use a rotary evaporator to remove the solvent , the obtained solid was dried and passed through a silica gel funnel, the volume ratio of dichloromethane: petroleum ether was 1:3 as the eluent, the filtrate was removed by a rotary evaporator, and the obtained solid was dried to obtain compound 298 (20.80 g, yield : 82%).

Reference： [1]Current Patent Assignee: JILIN OLODE OPTOELECTRONIC MAT - CN114685289, 2022, A Location in patent: Paragraph 0080-0081; 0084-0090

25
[ 500717-23-7 ]
[ 2826304-75-8 ]
[ 2826303-26-6 ]

Yield	Reaction Conditions	Operation in experiment
81%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tri-tert-butyl phosphine; sodium tertiary butoxide In toluene at 105℃; for 10h; Inert atmosphere;	4 Under the protection ofN2, the intermediate E-125 (about 37 mmol) and the reactant F-125 (44.4 mmol) were added to the reaction vessel after being dissolved in toluene (500 mL), Pd2(dba)3(0.37 mmol), P (t-Bu)3 was added(1.85mmol)t-BuONa(81.4mmol) Heat up to 105 °C after addition to the reaction for 10 h; Using diatomaceous earth while hot filtration, remove salts and catalysts, after the filtrate is cooled to room temperature, the solvent is removed using a rotary evaporator, the resulting solid is dried through a silicone funnel, tetrachloromethane is used as an eluent, the filtrate is removed with a rotary evaporator, the resulting solid is dried, and compound 125 (22.55g, yield: 81%).

Reference： [1]Current Patent Assignee: JILIN OLED OPTICAL AND ELECTRONIC MATERIALS CO LTD - CN114920657, 2022, A Location in patent: Paragraph 0152-0153; 0157-0158

26
[ 500717-23-7 ]
[ 2803310-99-6 ]
[ 2803310-25-8 ]

Yield	Reaction Conditions	Operation in experiment
86.1%	With Palladium⁽⁰⁾ bis(dibenzylideneacetone); sodium tertiary butoxide In toluene at 100℃; for 6h; Inert atmosphere;	14 Synthesis of compound C-14: Compound 5-4 (10 mmol), compound 14-1 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene under nitrogen atmosphere for 100 °C stirred for 6h. After cooling, the solvent was removed by rotary evaporation, extracted and washed with water to separate the liquids. Compound C-14 was obtained by organic phase column chromatography, yield: 86.1%.

Reference： [1]Current Patent Assignee: TCL TECHNOLOGY GROUP CORPORATION - CN114736180, 2022, A Location in patent: Paragraph 0197-0200

27
[ 500717-23-7 ]
[ 2850330-29-7 ]
[ 2850329-05-2 ]

Yield	Reaction Conditions	Operation in experiment
85%	With tris(1,5-diphenylpenta-1,4-dien-3-one)dipalladium; tri-tert-butyl phosphine; sodium tertiary butoxide In toluene at 120℃; for 12h; Inert atmosphere;	7 Intermediate M54 (4.76 g, 10.0 mmol), c54 (4.21 g, 10.5 mmol), tris(dibenzylideneacetone)dipalladium (0.18 g, 0.2 mmol), (1.92 g, 20 mmol) in sodium tert-butoxide . The reaction system was pumped and ventilated three times under nitrogen protection. Then, a toluene solution (1 mol/L) of tri-tert-butylphosphine (1 mol/L) and 30 ml of toluene were added (0.8 mL, 0.8 mmol) with a syringe. Under nitrogen protection, the mixture was heated and stirred at 120°C for reflux reaction for 12h. The reaction was stopped, cooled to room temperature, 100 ml of deionized water was added, and extracted three times with ethyl acetate. The solvent was removed by rotary evaporation, separated on a silica gel column, rinsed with dichloromethane/petroleum ether (1:10), the solvent was rotary dried, and vacuum-dried to obtain 6.78 g of the target product with a yield of 85%.

Reference： [1]Current Patent Assignee: ZHEJIANG HONGWU TECHNOLOGY CO LTD - CN115141173, 2022, A Location in patent: Paragraph 0064-0065; 0068

Same Skeleton Products

Related Products

Historical Records

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 500717-23-7 ] {[proInfo.proName]}

Quality Control of [ 500717-23-7 ]

Related Doc. of [ 500717-23-7 ]

Product Details of [ 500717-23-7 ]

Calculated chemistry of [ 500717-23-7 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 500717-23-7 ]

Application In Synthesis of [ 500717-23-7 ]

[ 500717-23-7 ] Synthesis Path-Upstream 1~3

[ 500717-23-7 ] Synthesis Path-Downstream 1~27

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry