[ CAS No. 1256823-65-0 ] {[proInfo.proName]}

Name: 1256823-65-0|5-Bromo-6-chloropicolinonitrile|97%
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SKU: A233615
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Quality Control of [ 1256823-65-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1256823-65-0 ]

SDS Specification

Alternatived Products of [ 1256823-65-0 ]

Product Details of [ 1256823-65-0 ]

CAS No. :	1256823-65-0	MDL No. :	MFCD18257828
Formula :	C₆H₂BrClN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	GKCQPDVYUJLEIJ-UHFFFAOYSA-N
M.W :	217.45	Pubchem ID :	71721353
Synonyms :

Calculated chemistry of [ 1256823-65-0 ]

Physicochemical Properties

Num. heavy atoms :	10
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 :	41.66
TPSA :	36.68 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) :	-5.81 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.73
Log Po/w (XLOGP3) :	2.56
Log Po/w (WLOGP) :	2.37
Log Po/w (MLOGP) :	1.16
Log Po/w (SILICOS-IT) :	2.65
Consensus Log Po/w :	2.09

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.24
Solubility :	0.124 mg/ml ; 0.000569 mol/l
Class :	Soluble
Log S (Ali) :	-2.98
Solubility :	0.229 mg/ml ; 0.00105 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.59
Solubility :	0.0564 mg/ml ; 0.000259 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.88

Safety of [ 1256823-65-0 ]

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

Application In Synthesis of [ 1256823-65-0 ]

* 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 [ 1256823-65-0 ]
Downstream synthetic route of [ 1256823-65-0 ]

[ 1256823-65-0 ] Synthesis Path-Upstream 1~3

1
[ 1256823-65-0 ]
[ 1214329-07-3 ]

Reference： [1] Patent: US2012/252758, 2012, A1,

2
[ 7677-24-9 ]
[ 1373126-39-6 ]
[ 1256823-65-0 ]

Yield	Reaction Conditions	Operation in experiment
67%	Stage #1: With N,N-Dimethylcarbamoyl chloride In dichloromethane for 72 h; Reflux Stage #2: With sodium hydrogencarbonate In dichloromethane; water	Step 2. Synthesis of 5-bromo-6-chloropyridine-2-carbonitrile (C28) Trimethylsilyl cyanide (19 mL, 0.15 mol) was added to a stirred solution of 3-bromo-2-chloropyridine 1-oxide (C27) (31.6 g, 0.152 mol) and triethylamine (63.4 mL, 0.46 mol) in acetonitrile (400 mL). The reaction mixture was heated to 50° C. for 2 hours. It was then cooled to room temperature and additional trimethylsilyl cyanide (19 mL, 0.15 mol) was added. After the reaction mixture was heated at 50° C. for 1.5 hours, a final portion of trimethylsilyl cyanide (28.5 mL, 0.23 mol) was added and the reaction was heated at reflux for 3 days. After dilution with dichloromethane (2 L), the reaction was washed with saturated aqueous sodium bicarbonate solution (800 mL), then with water (1 L), dried over magnesium sulfate and concentrated in vacuo. Purification via silica gel chromatography (Gradient: 20percent to 25percent ethyl acetate in heptane) afforded the title compound as a yellow solid. Yield: 14.92 g, 68.6 mmol, 45percent. The reaction was also performed using the acylating agent dimethylcarbamoyl chloride. A solution of dimethylcarbamoyl chloride (12.9 mL, 0.14 mol) in dichloromethane (23 mL) was added drop-wise to a stirred solution of 3-bromo-2-chloropyridine 1-oxide (C27) (11.23 g, 53.9 mmol) and trimethylsilyl cyanide (17.5 mL, 0.14 mol) in dichloromethane (200 mL). The reaction mixture was heated under reflux for 3 days, then diluted with dichloromethane (450 mL) and washed with saturated aqueous sodium bicarbonate solution (2*200 mL), then with water (200 mL), dried over magnesium sulfate and concentrated in vacuo. Purification via silica gel chromatography (Gradient: 15percent to 20percent ethyl acetate in heptane) provided the title compound, contaminated with dimethylcarbamoyl cyanide (12.73 g, 100percent) as an off-white solid.

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 8, p. 2906 - 2911
[2] Patent: US2012/252758, 2012, A1, . Location in patent: Page/Page column 28

3
[ 52200-48-3 ]
[ 1256823-65-0 ]

Reference： [1] Patent: US2012/252758, 2012, A1,

[ 1256823-65-0 ] Synthesis Path-Downstream 1~37

1
[ 67-56-1 ]
[ 1256823-65-0 ]
C₇H₆BrClN₂O [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 2906 - 2911

2
[ 7677-24-9 ]
[ 1373126-39-6 ]
[ 1256823-65-0 ]

Yield	Reaction Conditions	Operation in experiment
67%		Step 2. Synthesis of 5-bromo-6-chloropyridine-2-carbonitrile (C28) Trimethylsilyl cyanide (19 mL, 0.15 mol) was added to a stirred solution of 3-bromo-2-chloropyridine 1-oxide (C27) (31.6 g, 0.152 mol) and triethylamine (63.4 mL, 0.46 mol) in acetonitrile (400 mL). The reaction mixture was heated to 50 C. for 2 hours. It was then cooled to room temperature and additional trimethylsilyl cyanide (19 mL, 0.15 mol) was added. After the reaction mixture was heated at 50 C. for 1.5 hours, a final portion of trimethylsilyl cyanide (28.5 mL, 0.23 mol) was added and the reaction was heated at reflux for 3 days. After dilution with dichloromethane (2 L), the reaction was washed with saturated aqueous sodium bicarbonate solution (800 mL), then with water (1 L), dried over magnesium sulfate and concentrated in vacuo. Purification via silica gel chromatography (Gradient: 20% to 25% ethyl acetate in heptane) afforded the title compound as a yellow solid. Yield: 14.92 g, 68.6 mmol, 45%. The reaction was also performed using the acylating agent dimethylcarbamoyl chloride. A solution of dimethylcarbamoyl chloride (12.9 mL, 0.14 mol) in dichloromethane (23 mL) was added drop-wise to a stirred solution of 3-bromo-2-chloropyridine 1-oxide (C27) (11.23 g, 53.9 mmol) and trimethylsilyl cyanide (17.5 mL, 0.14 mol) in dichloromethane (200 mL). The reaction mixture was heated under reflux for 3 days, then diluted with dichloromethane (450 mL) and washed with saturated aqueous sodium bicarbonate solution (2*200 mL), then with water (200 mL), dried over magnesium sulfate and concentrated in vacuo. Purification via silica gel chromatography (Gradient: 15% to 20% ethyl acetate in heptane) provided the title compound, contaminated with dimethylcarbamoyl cyanide (12.73 g, 100%) as an off-white solid.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 2906 - 2911
[2]Patent: US2012/252758,2012,A1 .Location in patent: Page/Page column 28

3
[ 1256823-65-0 ]
[ 1241428-34-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 2906 - 2911

4
[ 1256823-65-0 ]
[ 1214337-82-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 2906 - 2911

5
[ 1256823-65-0 ]
[ 1373126-40-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 2906 - 2911
[2]Patent: US2012/252758,2012,A1

6
[ 1256823-65-0 ]
[ 1227082-74-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 2906 - 2911

7
[ 67-56-1 ]
[ 1256823-65-0 ]
[ 1402004-06-1 ]

Yield	Reaction Conditions	Operation in experiment
100%		Step 3. Synthesis of methyl 5-bromo-6-methoxypyridine-2-carboximidoate (C29) Sodium hydride (60% dispersion in mineral oil, 3.57 g, 93.8 mmol) was added portion-wise over a 20 minute period to a stirred solution of methanol (7.1 mL) in tetrahydrofuran (123 mL) under argon; the reaction was then stirred for an additional 55 minutes. A solution of <strong>[1256823-65-0]5-bromo-6-chloropyridine-2-carbonitrile</strong> (C28) (8.16 g, 37.5 mmol) in tetrahydrofuran (71 mL) was then added drop-wise and the reaction mixture was stirred for 18 hours. After being quenched with saturated aqueous ammonium chloride solution (200 mL), the mixture was extracted with ethyl acetate (2*400 mL). The combined organic layers were washed with saturated aqueous sodium chloride solution (200 mL), dried over magnesium sulfate and concentrated in vacuo to give the crude title compound (9.42 g, quantitative) as an orange solid, which was used in the next step without further purification, as it was found to be unstable on silica gel. LCMS m/z 247.1 (M+1). 1H NMR (400 MHz, CDCl3) delta 3.99 (s, 3H), 4.09 (s, 3H), 7.32 (d, J=7.8 Hz, 1H), 7.90 (d, J=7.8 Hz, 1H).

Reference： [1]Patent: US2012/252758,2012,A1 .Location in patent: Page/Page column 28-29

8
[ 1256823-65-0 ]
[ 1214329-07-3 ]