[ CAS No. 52208-50-1 ] {[proInfo.proName]}

Name: 52208-50-1|2,6-Dichloro-3-fluoropyridine|96%
Brand: Ambeed
SKU: A218284
Price: 10.0 USD
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Quality Control of [ 52208-50-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 52208-50-1 ]

SDS Specification

Alternatived Products of [ 52208-50-1 ]

Product Details of [ 52208-50-1 ]

CAS No. :	52208-50-1	MDL No. :	MFCD09907815
Formula :	C₅H₂Cl₂FN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YAXSIJLRAOURJK-UHFFFAOYSA-N
M.W :	165.98	Pubchem ID :	13290751
Synonyms :

Calculated chemistry of [ 52208-50-1 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	34.22
TPSA :	12.89 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.72 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.85
Log Po/w (XLOGP3) :	2.24
Log Po/w (WLOGP) :	2.95
Log Po/w (MLOGP) :	2.12
Log Po/w (SILICOS-IT) :	3.13
Consensus Log Po/w :	2.46

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.77
Solubility :	0.28 mg/ml ; 0.00168 mol/l
Class :	Soluble
Log S (Ali) :	-2.15
Solubility :	1.19 mg/ml ; 0.00714 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.53
Solubility :	0.0492 mg/ml ; 0.000296 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.77

Safety of [ 52208-50-1 ]

Signal Word:	Danger	Class:	8,6.1
Precautionary Statements:	P261-P280-P301+P310-P305+P351+P338	UN#:	2923
Hazard Statements:	H301-H315-H318-H335	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 52208-50-1 ]

* 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 [ 52208-50-1 ]
Downstream synthetic route of [ 52208-50-1 ]

[ 52208-50-1 ] Synthesis Path-Upstream 1~3

1
[ 52208-50-1 ]
[ 62476-56-6 ]

Reference： [1] Journal of Heterocyclic Chemistry, 1984, vol. 21, # 3, p. 673 - 679

2
[ 62476-56-6 ]
[ 52208-50-1 ]

Reference： [1] Heterocycles, 1993, vol. 36, # 3, p. 431 - 434

3
[ 16013-85-7 ]
[ 52208-50-1 ]

Reference： [1] Heterocycles, 1993, vol. 36, # 3, p. 431 - 434

[ 52208-50-1 ] Synthesis Path-Downstream 1~59

1
[ 62476-56-6 ]
[ 52208-50-1 ]

Reference： [1]Heterocycles,1993,vol. 36,p. 431 - 434

2
[ 124-38-9 ]
[ 52208-50-1 ]
2,6-dichloro-3-fluoropyridine-4-carboxylic acid [ No CAS ]

Reference： [1]Heterocycles,1993,vol. 36,p. 431 - 434

3
[ 52208-50-1 ]
[ 62476-56-6 ]
2-amino-6-chloro-3-fluoropyridine [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,1984,vol. 21,p. 673 - 679

4
2,6-dichloro-3-pyridinediazonium tetrafluoroborate [ No CAS ]
[ 52208-50-1 ]

Reference： [1]Journal of Heterocyclic Chemistry,1984,vol. 21,p. 673 - 679

5
[ 16013-85-7 ]
[ 52208-50-1 ]

Reference： [1]Heterocycles,1993,vol. 36,p. 431 - 434

Yield	Reaction Conditions	Operation in experiment
		Representative halopyridine compounds which can be prepared by the method of the present invention include: ... 2,5,6-tribromopyridine; 2,5,6-trifluoropyridine; 2,5-dichloro-6-fluoropyridine; 2,5-dichloro-6-bromopyridine; 2,6-dichloro-5-fluoropyridine; 2,6-dichloro-5-bromopyridine; 2,6-difluoro-5-chloropyridine; 2,6-dibromo-5-chloropyridine and ...

7
[ 1679-18-1 ]
[ 52208-50-1 ]
[ 1233697-21-6 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; water; at 20℃; for 18.0h;	A solution of 2.2 g 2,4-chloro-5-fluoropyridine, 2.28 g 4-chlorophenylboronic acid and 0.6 g tetrakistriphenylphosphinpalladium in 30 mL tetrahydrofuran was added 30 mL of a 10% a solution of potassium carbonate in water and the mixture was stirred at ambient temperature for 18 h. The reaction mixture was diluted with ethyl acetate and water. The phases were separated and the organic phase was washed water, 10% aqueous citric acid, 10% aqueous sodium bicarbonate and brine, dried over sodium sulfate and evaporated. The residue was purified by chromatography on silica gel with a gradient of heptane:dichloromethane=9:1 to 1:1 (only starting spot was removed) The product fractions were collected and evaporated. The residue was subjected to kugelrohr distillation at 0.03 mBar and 110 C. to yield 1.72 g of the title compound as colorless oil which solidified into white crystals, MS 241 and 243 (M+H)+.
	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; water; at 20℃; for 18.0h;	Example lOd6-Chloro-2-(4-chloro-phenyl)-3-fluoro-pyridineA solution of 2.2g 2,4-chloro-5-fluoropyridine, 2.28g 4-chlorophenylboronic acid and 0.6 g tetrakistriphenylphosphine palladium in 30 ml tetrahydrofuran was added 30 ml of a 10% a solution of potassium carbonate in water and the mixture was stirred at ambient temperature for 18h. The reaction mixture was diluted with ethyl acetate and water. The phases were separated and the organic phase was washed water, 10% aqueous citric acid, 10% aqueous sodium bicarbonate and brine, dried over sodium sulfate and evaporated. The residue was purified by chromatography on silica gel with a gradient of heptane : dichloromethane = 9 : 1 to 1 : 1 (only startspot was removed) The product fractions were collected and evaporated. The residue was subjected to Kugelrohr distillation at 0.03 mbar and 110 C to yield 1.72 g of the title compound as colorless oil which solidified into white crystals. MS (EI) (M+H): 241 and 243:

Reference： [1]Patent: US2012/65212,2012,A1 .Location in patent: Page/Page column 25
[2]Patent: WO2012/80144,2012,A1 .Location in patent: Page/Page column 47-48

8
[ 52208-50-1 ]
[ 1364677-55-3 ]

Reference： [1]Patent: US2012/65212,2012,A1

9
[ 52208-50-1 ]
[ 1364677-57-5 ]

Reference： [1]Patent: US2012/65212,2012,A1

10
[ 52208-50-1 ]
[ 1364677-59-7 ]

Reference： [1]Patent: US2012/65212,2012,A1

11
[ 1679-18-1 ]
[ 52208-50-1 ]
[ 1364677-55-3 ]
[ 1382465-66-8 ]

Reference： [1]Patent: WO2012/80144,2012,A1

12
[ 52208-50-1 ]
[ 216854-23-8 ]
[ 1527525-41-2 ]

Yield	Reaction Conditions	Operation in experiment
22%	With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine; In 1,4-dioxane; at 105℃;Inert atmosphere; Sealed tube;	A mixture of 2,6-dichloro-3-fluoro-pyridine (3.802 mmol, 631.1 mg), tert-butyl N-[(3S)-3-piperidyl]carbamate (3.992 mmol; 799.6 mg), potassium carbonate (7.605 mmol; 1051 mg),N,N?-Dimethylethylenediamine (0.3802 mmol; 33.52 mg; 0.0409 mL), and copper(I) iodide; (3.802 mmol; 724.1 mg) in 1,4-Dioxane (15 mL) was purged with Argon then sealed in a pressure tube and heated at 105C overnight. The reaction was cooled to room temperature, then filtered through Celite. The filtrate was concentrated and the residue was purified on silica eluted with 0 to 20% EtOAc in Heptane to afford tert-butyl N-[(3S)-1-(6-chloro-3-fluoro-2-pyridyl)-3-piperidyl]carbamate (279.2 mg, 22%) as a white solid.

Reference： [1]Patent: WO2014/1377,2014,A1 .Location in patent: Page/Page column 144

13
[ 52208-50-1 ]
[ 1527523-83-6 ]

Reference： [1]Patent: WO2014/1377,2014,A1

14
[ 52208-50-1 ]
[ 1527525-42-3 ]

Reference： [1]Patent: WO2014/1377,2014,A1

15
[ 52208-50-1 ]
[ 1609686-95-4 ]

Reference： [1]Patent: WO2014/72419,2014,A1
[2]Journal of Medicinal Chemistry,2016,vol. 59,p. 1854 - 1868

16
[ 52208-50-1 ]
[ 1609686-81-8 ]
[ 1609687-21-9 ]

Reference： [1]Patent: WO2014/72419,2014,A1
[2]Journal of Medicinal Chemistry,2016,vol. 59,p. 1854 - 1868

17
[ 52208-50-1 ]
[ 873-74-5 ]
[ 1609687-10-6 ]

Yield	Reaction Conditions	Operation in experiment
89%	With palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; sodium t-butanolate; In 1,4-dioxane; at 110℃; for 16.0h;Inert atmosphere;	General procedure: Stock solution of 5 mol% Pd catalyst in dioxane was prepared as follows. A flask was charged with Pd(OAc)2 (0.025 mmol, 5.6 mg) and Xantphos (0.03 mmol, 17 mg); dry dioxane (5 mL) was added and the resulting solution was stirred for 15 min under an argon atmosphere. Next, a 50 mL round bottomed flask was charged with 2,5-dichloro-5-fluoropyridine (0.5 mmol, 83 mg), an aniline 2 (0.6 mmol) and t- BuONa (0.7 mmol, 67 mg). Freshly prepared stock solution of Pd catalyst was added and the resulting solution was stirred for 2 min under an argon atmosphere. The round bottomed flask was kept in 110 C preheated oil bath and reaction mixture was refluxed for 16 h, then allowed to cool down to room temperature and filtered through Celite. Celite cake was washed with 100 mL dichloromethane, combined organic phases were evaporated to dryness under reduced pressure and the residue separated with an automated chromatography system using Silica Flash Cartridges applying a heptane-ethyl acetate gradient (from 100% heptane to 100% ethylacetate in 35 minutes, 35 mL/min).

Reference： [1]Patent: WO2014/72419,2014,A1 .Location in patent: Page/Page column 16; 27; 29
[2]Journal of Medicinal Chemistry,2016,vol. 59,p. 1854 - 1868

18
[ 52208-50-1 ]
[ 619-45-4 ]
[ 1609687-14-0 ]

Yield	Reaction Conditions	Operation in experiment
66%	With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 110℃; for 16.0h;Inert atmosphere;	Stock solution of 5 mol% Pd catalyst in dioxane was prepared as follows. A flask was charged with Pd(OAc)2 (0.025 mmol, 5.6 mg) and Xantphos (0.03 mmol, 17 mg); dry dioxane (5 mL) was added and the resulting solution was stirred for 15 min under an argon atmosphere. Next, a 50 mL round bottomed flask was charged with 2,5-dichloro-5-fluoropyridine (0.5 mmol, 83 mg), an aniline 2 (0.6 mmol) and t- BuONa (0.7 mmol, 67 mg). Freshly prepared stock solution of Pd catalyst was added and the resulting solution was stirred for 2 min under an argon atmosphere. The round bottomed flask was kept in 110 C preheated oil bath and reaction mixture was refluxed for 16 h, then allowed to cool down to room temperature and filtered through Celite. Celite cake was washed with 100 mL dichloromethane, combined organic phases were evaporated to dryness under reduced pressure and the residue separated with an automated chromatography system using Silica Flash Cartridges applying a heptane-ethyl acetate gradient (from 100% heptane to 100% ethylacetate in 35 minutes, 35 mL/min). The general procedure B was followed using Pd(OAc)2 (0.1 mmol, 22 mg), xantphos (0.120 mmol, 0.069 g), 2,5-dichloro-5- fluoropyridine (2.0 mmol, 0.332 g), methyl 4-aminobenzoate (2.0 mmol, 0.302 g) and Cs2C03 (10.0 mmol, 3.26 g). white solid; yield 66% (0.367 g); mp 159-160 C; H NMR (400 MHz, CDCI3): 5 3.89 (s, 3H), 6.78 (dd, J = 8.2 Hz, 2.8 Hz, 1 H), 6.83 (brs, 1 H), 7.27 (dd, J = 8.2 Hz, 9.9 Hz, 1 H), 7.71 (d, J = 8.8 Hz, 2H), 8.02 (d, J = 8.8 Hz, 2H).

Reference： [1]Patent: WO2014/72419,2014,A1 .Location in patent: Page/Page column 27; 29; 30
[2]Journal of Medicinal Chemistry,2016,vol. 59,p. 1854 - 1868

19
[ 22072-33-9 ]
[ 52208-50-1 ]
[ 1609687-13-9 ]
[ 1609687-33-3 ]

Yield	Reaction Conditions	Operation in experiment
	With palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; sodium t-butanolate; In 1,4-dioxane; at 110℃; for 16.0h;Inert atmosphere;	General procedure: Stock solution of 5 mol% Pd catalyst in dioxane was prepared as follows. A flask was charged with Pd(OAc)2 (0.025 mmol, 5.6 mg) and Xantphos (0.03 mmol, 17 mg); dry dioxane (5 mL) was added and the resulting solution was stirred for 15 min under an argon atmosphere. Next, a 50 mL round bottomed flask was charged with 2,5-dichloro-5-fluoropyridine (0.5 mmol, 83 mg), an aniline 2 (0.6 mmol) and t- BuONa (0.7 mmol, 67 mg). Freshly prepared stock solution of Pd catalyst was added and the resulting solution was stirred for 2 min under an argon atmosphere. The round bottomed flask was kept in 110 C preheated oil bath and reaction mixture was refluxed for 16 h, then allowed to cool down to room temperature and filtered through Celite. Celite cake was washed with 100 mL dichloromethane, combined organic phases were evaporated to dryness under reduced pressure and the residue separated with an automated chromatography system using Silica Flash Cartridges applying a heptane-ethyl acetate gradient (from 100% heptane to 100% ethylacetate in 35 minutes, 35 mL/min).

Reference： [1]Patent: WO2014/72419,2014,A1 .Location in patent: Page/Page column 27; 29; 30
[2]Journal of Medicinal Chemistry,2016,vol. 59,p. 1854 - 1868

20
[ 52208-50-1 ]
[ 1609686-75-0 ]