[ CAS No. 1211523-71-5 ] {[proInfo.proName]}

Name: 1211523-71-5|2-(2-Bromopyridin-3-yl)acetonitrile|95%
Brand: Ambeed
SKU: A100660
Price: 79.0 USD
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Quality Control of [ 1211523-71-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1211523-71-5 ]

SDS Specification

Alternatived Products of [ 1211523-71-5 ]

Product Details of [ 1211523-71-5 ]

CAS No. :	1211523-71-5	MDL No. :	MFCD10000072
Formula :	C₇H₅BrN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ZELUAAXEWIYSLH-UHFFFAOYSA-N
M.W :	197.03	Pubchem ID :	53403509
Synonyms :

Calculated chemistry of [ 1211523-71-5 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	41.46
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) :	-6.42 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.48
Log Po/w (XLOGP3) :	1.53
Log Po/w (WLOGP) :	1.91
Log Po/w (MLOGP) :	0.89
Log Po/w (SILICOS-IT) :	2.31
Consensus Log Po/w :	1.62

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.4
Solubility :	0.778 mg/ml ; 0.00395 mol/l
Class :	Soluble
Log S (Ali) :	-1.91
Solubility :	2.43 mg/ml ; 0.0123 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-3.37
Solubility :	0.0837 mg/ml ; 0.000425 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.86

Safety of [ 1211523-71-5 ]

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 [ 1211523-71-5 ]

* 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 [ 1211523-71-5 ]
Downstream synthetic route of [ 1211523-71-5 ]

[ 1211523-71-5 ] Synthesis Path-Upstream 1~7

1
[ 773837-37-9 ]
[ 1307248-71-0 ]
[ 1211523-71-5 ]

Yield	Reaction Conditions	Operation in experiment
95%	at 20℃; Inert atmosphere	A solution of (2-bromopyridin-3-yl) methyl methanesulfonate 2 (200 mg, 0.75 mmol) and NaCN (0.18 g, 3.75 mmol) in DMSO (2 mL) was stirred overnight at room temperature. Ethylacetate (10 mL) was then added. The resulting solution was washed with water (3X10 mL) then extracted with ethylacetate (3X10 mL). The organic layer was dried over MgSO4 then evaporated to yield a brown oil which was filtered through a short pad of silica with diethylether to give compound 3 as white crystals (95percent).

Reference： [1] Tetrahedron Letters, 2011, vol. 52, # 22, p. 2876 - 2880

2
[ 5697-44-9 ]
[ 128071-75-0 ]
[ 1211523-71-5 ]

Yield	Reaction Conditions	Operation in experiment
2.21 g	Stage #1: With potassium <i>tert</i>-butylate In 1,2-dimethoxyethane at -60℃; for 1 h; Stage #2: With methanol In 1,2-dimethoxyethane at 20 - 85℃; for 2 h;	To a -60 °C mixture of t-BuOK (5.92 g, 52.76 mmol) in 1,2-dimethoxyethane (50 mL)was added a solution of 2-tosylacetonitrile (5.08 g, 26.02 mmol) in 1,2-dimethoxyethane (20 mL)dropwise. To the resulting mixture was added a solution of 2-bromonicotinaldehyde (4.81 g, 25.86 mmol) in 1 ,2-dimethoxyethane (20 mL) dropwise at -60 °C. After stirring for 1 h at thistemperature, MeOH was added (50 mL), the resulting mixture was allowed to warm to RT, stirred for 1 h and warmed to 85 °C, stirred for another lh. After cooling to RT, the volatiles was removedunder reduced pressure, diluted with brine (200 mL) and extracted with EA (3 x 150 mL). Thecombined organic layers were dried over anhydrous Na2504, filtered and concentrated underreduced pressure. The residue was purified by silica chromatography (eluting with EA: Hex = 1:10, v/v) to give 2-(2-bromopyridin-3-yl)acetonitrile (2.21 g). MS: m/z 197 (M+H) .

Reference： [1] Patent: WO2018/172984, 2018, A1, . Location in patent: Page/Page column 67

3
[ 773837-37-9 ]
[ 94446-97-6 ]
[ 1211523-71-5 ]

Reference： [1] Patent: US2011/118251, 2011, A1, . Location in patent: Page/Page column 16

4
[ 131747-54-1 ]
[ 1211523-71-5 ]

Reference： [1] Patent: US2011/118251, 2011, A1,
[2] Tetrahedron Letters, 2011, vol. 52, # 22, p. 2876 - 2880
[3] Chemistry - A European Journal, 2012, vol. 18, # 15, p. 4480 - 4484

5
[ 94446-97-6 ]
[ 1211523-71-5 ]

Reference： [1] Organic and Biomolecular Chemistry, 2012, vol. 10, # 31, p. 6404 - 6409

6
[ 7677-24-9 ]
[ 94446-97-6 ]
[ 1211523-71-5 ]

Reference： [1] Chemistry - A European Journal, 2012, vol. 18, # 15, p. 4480 - 4484

7
[ 128071-75-0 ]
[ 1211523-71-5 ]

Reference： [1] Patent: US2011/118251, 2011, A1,
[2] Chemistry - A European Journal, 2012, vol. 18, # 15, p. 4480 - 4484

[ 1211523-71-5 ] Synthesis Path-Downstream 1~23

1
[ 128071-75-0 ]
[ 1211523-71-5 ]

Reference： [1]Patent: US2011/118251,2011,A1
[2]Chemistry - A European Journal,2012,vol. 18,p. 4480 - 4484

2
[ 131747-54-1 ]
[ 1211523-71-5 ]

Reference： [1]Patent: US2011/118251,2011,A1
[2]Tetrahedron Letters,2011,vol. 52,p. 2876 - 2880
[3]Chemistry - A European Journal,2012,vol. 18,p. 4480 - 4484

3
[ 773837-37-9 ]
[ 94446-97-6 ]
[ 1211523-71-5 ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; water; for 1h;Reflux;	PREPARATION 322-(2-Bromo-3-pyridyl)acetonitrile; A mixture of 2-bromo-3-bromomethyl-pyridine (840 mg, 3.35 mmol) and sodium cyanide (187.99 mg, 3.68 mmol) is stirred and refluxed for 1 h in a mixture water (10 mL)-ethanol (2 mL). The reaction mixture is diluted with dichloromethane and washed with saturated aqueous solution of sodium bicarbonate. The organic layer is separated, dried over magnesium sulfate and the solvent evaporated in vacuo to give 83% of the title compound that is used without further purification. MS (m/z): 197 (M+1), 199 (M+3).

Reference： [1]Patent: US2011/118251,2011,A1 .Location in patent: Page/Page column 16

4
[ 773837-37-9 ]
[ 1307248-71-0 ]
[ 1211523-71-5 ]

Yield	Reaction Conditions	Operation in experiment
95%	In dimethyl sulfoxide; at 20℃;Inert atmosphere;	A solution of (2-bromopyridin-3-yl) methyl methanesulfonate 2 (200 mg, 0.75 mmol) and NaCN (0.18 g, 3.75 mmol) in DMSO (2 mL) was stirred overnight at room temperature. Ethylacetate (10 mL) was then added. The resulting solution was washed with water (3X10 mL) then extracted with ethylacetate (3X10 mL). The organic layer was dried over MgSO4 then evaporated to yield a brown oil which was filtered through a short pad of silica with diethylether to give compound 3 as white crystals (95%).

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 2876 - 2880

5
[ 1211523-71-5 ]
[ 1310552-76-1 ]

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 2876 - 2880

6
[ 1211523-71-5 ]
[ 1310552-77-2 ]

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 2876 - 2880

7
[ 1211523-71-5 ]
[ 1310552-85-2 ]

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 2876 - 2880

8
[ 1211523-71-5 ]
2-(2-bromopyridin-3-yl) ethanamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With aluminum (III) chloride; lithium aluminium tetrahydride; In tetrahydrofuran; for 1h;Inert atmosphere;	In a three-necked flask equipped with a reflux condenser, lithium and aluminium hydride(1.95 mmol) was dissolved in anhydrous THF (2 mL). In a dropping funnel, aluminum chloride(1.95 mmol) dissolved in THF (3 mL) was added rapidly to the hydride solution. After five minutes, a solution of <strong>[1211523-71-5]2-(2-bromopyridin-3-yl) acetonitrile</strong> (1.77 mmol) in THF (4 mL) was added dropwise. One hour later, diethylether (40 mL) was added before adding a solution of 6 N sulphuric acid to reach an acidic pH. The mixture was extracted with diethylether. The pH of the aqueous layer was adjusted to 12 then extracted again with diethylether. The organic layer was dried then evaporated to afford a yellow oil (50%).

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 2876 - 2880

9
[ 75-30-9 ]
[ 1211523-71-5 ]
[ 1380541-23-0 ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 4480 - 4484

10
[ 1211523-71-5 ]
(5S,6S)-5-isopropyl-6-methyl-6,7-dihydro-5H-cyclopenta[b]pyridine-5-carbonitrile [ No CAS ]
[ 1380541-24-1 ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 4480 - 4484

11
[ 7677-24-9 ]
[ 94446-97-6 ]
[ 1211523-71-5 ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 4480 - 4484

12
potassium cyanide [ No CAS ]
[ 94446-97-6 ]
[ 1211523-71-5 ]

Reference： [1]Organic and Biomolecular Chemistry,2012,vol. 10,p. 6404 - 6409

13
[ 1211523-71-5 ]
[ 74-88-4 ]
[ 1393491-78-5 ]

Reference： [1]Organic and Biomolecular Chemistry,2012,vol. 10,p. 6404 - 6409

14
[ 1211523-71-5 ]
methyl 2-(4-methoxybenzyloxy)benzodithioate [ No CAS ]
C₂₂H₁₆BrN₂O₂S^(1-)*Na⁽¹⁺⁾ [ No CAS ]