[ CAS No. 1079179-12-6 ] {[proInfo.proName]}

Name: 1079179-12-6|2-Chloro-3-fluoro-5-nitropyridine|98%
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SKU: A302101
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Quality Control of [ 1079179-12-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1079179-12-6 ]

SDS Specification

Alternatived Products of [ 1079179-12-6 ]

Product Details of [ 1079179-12-6 ]

CAS No. :	1079179-12-6	MDL No. :	MFCD16659664
Formula :	C₅H₂ClFN₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SHXURKRHCSAERA-UHFFFAOYSA-N
M.W :	176.53	Pubchem ID :	52982879
Synonyms :

Calculated chemistry of [ 1079179-12-6 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	38.03
TPSA :	58.71 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.14 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.16
Log Po/w (XLOGP3) :	1.74
Log Po/w (WLOGP) :	2.2
Log Po/w (MLOGP) :	1.12
Log Po/w (SILICOS-IT) :	0.37
Consensus Log Po/w :	1.32

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.37
Solubility :	0.756 mg/ml ; 0.00428 mol/l
Class :	Soluble
Log S (Ali) :	-2.59
Solubility :	0.454 mg/ml ; 0.00257 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.3
Solubility :	0.887 mg/ml ; 0.00502 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	3.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.13

Safety of [ 1079179-12-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1079179-12-6 ]

* 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 [ 1079179-12-6 ]
Downstream synthetic route of [ 1079179-12-6 ]

[ 1079179-12-6 ] Synthesis Path-Upstream 1~2

1
[ 1033202-14-0 ]
[ 1079179-12-6 ]

Yield	Reaction Conditions	Operation in experiment
97%	at 60℃; for 10 h;	To a stirred solution of 3-fluoro-5-nitropyridin-2-ol (1.5 g, 9.48 mmol) in phosphorous oxychloride (15 ml_) was added phosphorous pentachloride (2.96 g, 14.22 mmol) at 60 °C. The reaction mixture was allowed to stir for 10h at the same temperature. The reaction mixture was cooled to ambient temperature and was poured into crushed ice and was extracted with ethyl acetate (3 x 20 mL). The total organic layer was washed with saturated sodium carbonate solution (25 ml_).The washed organic layer was dried over anhydrous magnesium sulfate and was concentrated under reduced pressure to obtain crude compound which was purified by using silica gel column chromatography (100-200 mesh, 5 percent ethyl acetate in hexane) to afford 2-chloro-3-fluoro-5-nitropyridine (1.62 g, 97 percent).
97%	at 60℃; for 10 h;	To a stirred solution of 3-fluoro-5-nitropyridin-2-ol (1.5 g, 9.48 mmol) in phosphorous oxychloride (15 mL) was added phosphorous pentachloride (2.96 g, 14.22 mmol) at 60 °C. The reaction mixture was allowed to stir for 10 h at the same temperature. The reaction mixture was cooled to room temperature and was poured into crushed ice and was extracted with ethyl acetate (3 x 20 mL). The total organic layer was washed with saturated sodium carbonate solution (25 mL). The washed organic layer was dried over anhydrous magnesium sulphate and was concentrated under reduced pressure to obtain crude compound which was purified by using column chromatography (silica gel: 100-200 mesh, eluent: 5 percent ethyl acetate in n-hexane) to afford 2-chloro-3-fluoro-5-nitropyridine (1.62 g, 97 percent).
97%	With phosphorus pentachloride; trichlorophosphate In hexane; ethyl acetate at 60℃; for 10 h;	Step 1: To a stirred solution of 3-fluoro-5-nitropyridin-2-ol (1.5 g, 9.48 mmol) in phosphorous oxychloride (15 mL) was added phosphorous pentachloride (2.96 g, 14.22 mmol) at 60° C. The reaction mixture was allowed to stir for 10 h at the same temperature. The reaction mixture was cooled to ambient temperature and was poured into crushed ice and was extracted with ethyl acetate (3*20 mL). The total organic layer was washed with saturated sodium carbonate solution (25 mL). The washed organic layer was dried over anhydrous magnesium sulfate and was concentrated under reduced pressure to obtain crude compound which was purified by using silica gel column chromatography (100-200 mesh, 5percent ethyl acetate in hexane) to afford 2-chloro-3-fluoro-5-nitropyridine (1.62 g, 97percent).

97%

With phosphorus pentachloride; trichlorophosphate In hexane at 60℃; for 10 h;

Step 1
To a stirred solution of 3-fluoro-5-nitropyridin-2-ol (1.5 g, 9.48 mmol) in phosphorous oxychloride (15 mL) was added phosphorous pentachloride (2.96 g, 14.22 mmol) at 60° C.
The reaction mixture was allowed to stir for 10 h at the same temperature.
The reaction mixture was cooled to room temperature and was poured into crushed ice and was extracted with ethyl acetate (3*20 mL).
The total organic layer was washed with saturated sodium carbonate solution (25 mL).
The washed organic layer was dried over anhydrous magnesium sulfate and was concentrated under reduced pressure to obtain crude compound which was purified by using column chromatography (silica gel: 100-200 mesh, eluent: 5percent ethyl acetate in n-hexane) to afford 2-chloro-3-fluoro-5-nitropyridine (1.62 g, 97percent).

Reference： [1] Patent: WO2013/13817, 2013, A1, . Location in patent: Page/Page column 96; 97
[2] Patent: WO2013/13815, 2013, A1, . Location in patent: Page/Page column 131
[3] Patent: US2013/29961, 2013, A1, . Location in patent: Paragraph 0656
[4] Patent: US2013/29962, 2013, A1, . Location in patent: Paragraph 0761
[5] MedChemComm, 2016, vol. 7, # 5, p. 1022 - 1032

2
[ 1547-29-1 ]
[ 1079179-12-6 ]

Reference： [1] MedChemComm, 2016, vol. 7, # 5, p. 1022 - 1032

[ 1079179-12-6 ] Synthesis Path-Downstream 1~31

1
[ 1079179-12-6 ]
[ 1419602-62-2 ]

Reference： [1]Patent: WO2013/13817,2013,A1
[2]Patent: WO2013/13815,2013,A1
[3]Patent: US2013/29961,2013,A1
[4]Patent: US2013/29962,2013,A1

2
[ 1079179-12-6 ]
[ 1419602-63-3 ]

Reference： [1]Patent: WO2013/13817,2013,A1
[2]Patent: WO2013/13815,2013,A1
[3]Patent: US2013/29961,2013,A1
[4]Patent: US2013/29962,2013,A1

3
[ 1079179-12-6 ]
[ 1419602-65-5 ]

Reference： [1]Patent: WO2013/13817,2013,A1
[2]Patent: WO2013/13815,2013,A1
[3]Patent: US2013/29961,2013,A1
[4]Patent: US2013/29962,2013,A1

4
[ 1079179-12-6 ]
[ 1421472-14-1 ]

Reference： [1]Patent: WO2013/13817,2013,A1
[2]Patent: US2013/29961,2013,A1

5
[ 1079179-12-6 ]
[ 7486-35-3 ]
[ 1419602-60-0 ]

Yield	Reaction Conditions	Operation in experiment
96%	With tris-(dibenzylideneacetone)dipalladium(0); In tetrahydrofuran; at 60℃; for 6h;Inert atmosphere;	To a stirred solution of <strong>[1079179-12-6]2-chloro-3-fluoro-5-nitropyridine</strong> (1.6 g, 9.0 mmol) in tetrahydrofuran (16 mL) was added tributylvinyltin (3.42 g, 10.8 mmol) and Pd2(dba) 3 (0.42 g, 0.45 mmol), trifuryl phosphene (0.2 g, 0.9 mmol) under nitrogen atmosphere. The reaction mixture was deoxygenated thoroughly and was heated to 60 C for 6 h. The reaction mixture was diluted with water (20 mL) and was extracted with ethyl acetate (3 x 25 mL). The combined organic layer was washed with brine (25 mL) and dried over anhydrous magnesium sulfate and concentrated under reduced pressure to afford the crude compound. The crude compound was purified by column chromatography (silica gel: 100-200 mesh; eluent: 5 % ethyl acetate in hexane) to afford 3-fluoro-5-nitro-2-vinylpyridine. (1.5 g, 96 %).
96%	With tris-(dibenzylideneacetone)dipalladium(0); In tetrahydrofuran; at 60℃; for 6h;Inert atmosphere;	To a stirred solution of <strong>[1079179-12-6]2-chloro-3-fluoro-5-nitropyridine</strong> (1.6 g, 9.0 mmol) in tetrahydrofuran (16 mL) under nitrogen atmosphere were added tributylvinyl tin (3.42 g, 10.8 mmol), Pd2(dba)3 (0.42 g, 0.45 mmol) and trifuryl phosphene (0.2 g, 0.9 mmol). The reaction mixture was deoxygenated thoroughly and was heated to 60 C for 6 h. The reaction mixture was diluted with water (20 mL) and extracted with ethyl acetate (3 x 25 mL). The combined organic layer was washed with brine (25 mL) and dried over anhydrous magnesium sulphate and concentrated under reduced pressure to afford the crude compound. The crude compound was purified by column chromatography (silica gel: 100-200 mesh; eluent: 5 % ethyl acetate in n-hexane) to afford 3-fluoro-5-nitro-2-vinylpyridine (1.5 g, 96 %).
96%	With tris-(dibenzylideneacetone)dipalladium(0); In tetrahydrofuran; at 60℃; for 6h;Inert atmosphere;	Step 2: To a stirred solution of <strong>[1079179-12-6]2-chloro-3-fluoro-5-nitropyridine</strong> (1.6 g, 9.0 mmol) in tetrahydrofuran (16 mL) was added tributylvinyltin (3.42 g, 10.8 mmol) and Pd2(dba)3 (0.42 g, 0.45 mmol), trifuryl phosphene (0.2 g, 0.9 mmol) under nitrogen atmosphere. The reaction mixture was deoxygenated thoroughly and was heated to 60 C. for 6 h. The reaction mixture was diluted with water (20 mL) and was extracted with ethyl acetate (3*25 mL). The combined organic layer was washed with brine (25 mL) and dried over anhydrous magnesium sulfate and concentrated under reduced pressure to afford the crude compound. The crude compound was purified by column chromatography (silica gel: 100-200 mesh; eluent: 5% ethyl acetate in hexane) to afford 3-fluoro-5-nitro-2-vinylpyridine. (1.5 g, 96%).

96%

With tris-(dibenzylideneacetone)dipalladium(0); trifuran-2-yl-phosphane; In tetrahydrofuran; at 60℃; for 6h;Inert atmosphere;

Step 2 To a stirred solution of <strong>[1079179-12-6]2-chloro-3-fluoro-5-nitropyridine</strong> (1.6 g, 9.0 mmol) in tetrahydrofuran (16 mL) under nitrogen atmosphere were added tributylvinyl tin (3.42 g, 10.8 mmol), Pd2(dba)3 (0.42 g, 0.45 mmol) and trifuryl phosphene (0.2 g, 0.9 mmol). The reaction mixture was deoxygenated thoroughly and was heated to 60 C. for 6 h. The reaction mixture was diluted with water (20 mL) and extracted with ethyl acetate (3*25 mL). The combined organic layer was washed with brine (25 mL) and dried over anhydrous magnesium sulfate and concentrated under reduced pressure to afford the crude compound. The crude compound was purified by column chromatography (silica gel: 100-200 mesh; eluent: 5% ethyl acetate in n-hexane) to afford 3-fluoro-5-nitro-2-vinylpyridine (1.5 g, 96%).

Reference： [1]Patent: WO2013/13817,2013,A1 .Location in patent: Page/Page column 97
[2]Patent: WO2013/13815,2013,A1 .Location in patent: Page/Page column 131; 132
[3]Patent: US2013/29961,2013,A1 .Location in patent: Paragraph 0657
[4]Patent: US2013/29962,2013,A1 .Location in patent: Paragraph 0762

6
[ 1079179-12-6 ]
[ 1419597-57-1 ]

Reference： [1]Patent: WO2013/13815,2013,A1
[2]Patent: US2013/29962,2013,A1

7
[ 1033202-14-0 ]
[ 1079179-12-6 ]

Yield	Reaction Conditions	Operation in experiment
97%	With phosphorus pentachloride; trichlorophosphate; at 60℃; for 10h;	To a stirred solution of 3-fluoro-5-nitropyridin-2-ol (1.5 g, 9.48 mmol) in phosphorous oxychloride (15 ml_) was added phosphorous pentachloride (2.96 g, 14.22 mmol) at 60 C. The reaction mixture was allowed to stir for 10h at the same temperature. The reaction mixture was cooled to ambient temperature and was poured into crushed ice and was extracted with ethyl acetate (3 x 20 mL). The total organic layer was washed with saturated sodium carbonate solution (25 ml_).The washed organic layer was dried over anhydrous magnesium sulfate and was concentrated under reduced pressure to obtain crude compound which was purified by using silica gel column chromatography (100-200 mesh, 5 % ethyl acetate in hexane) to afford 2-chloro-3-fluoro-5-nitropyridine (1.62 g, 97 %).
97%	With phosphorus pentachloride; trichlorophosphate; at 60℃; for 10h;	To a stirred solution of 3-fluoro-5-nitropyridin-2-ol (1.5 g, 9.48 mmol) in phosphorous oxychloride (15 mL) was added phosphorous pentachloride (2.96 g, 14.22 mmol) at 60 C. The reaction mixture was allowed to stir for 10 h at the same temperature. The reaction mixture was cooled to room temperature and was poured into crushed ice and was extracted with ethyl acetate (3 x 20 mL). The total organic layer was washed with saturated sodium carbonate solution (25 mL). The washed organic layer was dried over anhydrous magnesium sulphate and was concentrated under reduced pressure to obtain crude compound which was purified by using column chromatography (silica gel: 100-200 mesh, eluent: 5 % ethyl acetate in n-hexane) to afford 2-chloro-3-fluoro-5-nitropyridine (1.62 g, 97 %).
97%	With phosphorus pentachloride; trichlorophosphate; In hexane; ethyl acetate; at 60℃; for 10h;	Step 1: To a stirred solution of 3-fluoro-5-nitropyridin-2-ol (1.5 g, 9.48 mmol) in phosphorous oxychloride (15 mL) was added phosphorous pentachloride (2.96 g, 14.22 mmol) at 60 C. The reaction mixture was allowed to stir for 10 h at the same temperature. The reaction mixture was cooled to ambient temperature and was poured into crushed ice and was extracted with ethyl acetate (3*20 mL). The total organic layer was washed with saturated sodium carbonate solution (25 mL). The washed organic layer was dried over anhydrous magnesium sulfate and was concentrated under reduced pressure to obtain crude compound which was purified by using silica gel column chromatography (100-200 mesh, 5% ethyl acetate in hexane) to afford 2-chloro-3-fluoro-5-nitropyridine (1.62 g, 97%).

97%

With phosphorus pentachloride; trichlorophosphate; In hexane; at 60℃; for 10h;

Step 1 To a stirred solution of 3-fluoro-5-nitropyridin-2-ol (1.5 g, 9.48 mmol) in phosphorous oxychloride (15 mL) was added phosphorous pentachloride (2.96 g, 14.22 mmol) at 60 C. The reaction mixture was allowed to stir for 10 h at the same temperature. The reaction mixture was cooled to room temperature and was poured into crushed ice and was extracted with ethyl acetate (3*20 mL). The total organic layer was washed with saturated sodium carbonate solution (25 mL). The washed organic layer was dried over anhydrous magnesium sulfate and was concentrated under reduced pressure to obtain crude compound which was purified by using column chromatography (silica gel: 100-200 mesh, eluent: 5% ethyl acetate in n-hexane) to afford 2-chloro-3-fluoro-5-nitropyridine (1.62 g, 97%).

Reference： [1]Patent: WO2013/13817,2013,A1 .Location in patent: Page/Page column 96; 97
[2]Patent: WO2013/13815,2013,A1 .Location in patent: Page/Page column 131
[3]Patent: US2013/29961,2013,A1 .Location in patent: Paragraph 0656
[4]Patent: US2013/29962,2013,A1 .Location in patent: Paragraph 0761
[5]MedChemComm,2016,vol. 7,p. 1022 - 1032

8
[ 1079179-12-6 ]
[ 100243-39-8 ]
(S)-1-(3-fluoro-5-nitropyridin-2-yl)pyrrolidin-3-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%		Preparation 59 (S)-1-(3-Fluoro-5-nitropyridin-2-yl)pyrrolidin-3-ol To a mixture of NaH (227 mg, 5.68 mmol, 60%) in DME (30 mL) was added (S)-pyrrolidin-3-ol (494 mg, 5.68 mmol) and the reaction was stirred at room temperature for 1 hour. A solution of 2-chloro-4-fluoro-5-nitropyridine (250 mg, 1.42 mmol) in DME (10 mL) was added at 10 C. and stirred at room temperature for 1 hour. The reaction was quenched with water (30 mL) and extracted with EtOAc (100 mL*2). The organic layers were combined, concentrated in vacuo and purified by silica gel column chromatography eluting with 0-50% EtOAc in petroleum ether to afford the title compound (250 mg, 77%) as yellow solid. The following preparations were prepared according to the method described by Preparation 59 using the appropriate fluoropyridine as described.

Reference： [1]Patent: US2016/52930,2016,A1 .Location in patent: Paragraph 0630

9
[ 1079179-12-6 ]
(S)-1-(5-amino-3-fluoropyridin-2-yl)pyrrolidin-3-ol [ No CAS ]

Reference： [1]Patent: US2016/52930,2016,A1

10
[ 1547-29-1 ]
[ 1079179-12-6 ]