[ CAS No. 1201924-31-3 ] {[proInfo.proName]}

Name: 1201924-31-3|6-Chloro-3-methylpicolinonitrile|97%
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3d Animation Molecule Structure of 1201924-31-3

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Quality Control of [ 1201924-31-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1201924-31-3 ]

SDS Specification

Alternatived Products of [ 1201924-31-3 ]

Product Details of [ 1201924-31-3 ]

CAS No. :	1201924-31-3	MDL No. :	MFCD16658734
Formula :	C₇H₅ClN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	GRLXSZKHRDKVTE-UHFFFAOYSA-N
M.W :	152.58	Pubchem ID :	46856278
Synonyms :

Calculated chemistry of [ 1201924-31-3 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	38.93
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) :	-5.65 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.76
Log Po/w (XLOGP3) :	2.23
Log Po/w (WLOGP) :	1.92
Log Po/w (MLOGP) :	0.73
Log Po/w (SILICOS-IT) :	2.4
Consensus Log Po/w :	1.81

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.63
Solubility :	0.354 mg/ml ; 0.00232 mol/l
Class :	Soluble
Log S (Ali) :	-2.64
Solubility :	0.353 mg/ml ; 0.00231 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.1
Solubility :	0.122 mg/ml ; 0.0008 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.92

Safety of [ 1201924-31-3 ]

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

Application In Synthesis of [ 1201924-31-3 ]

* 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 [ 1201924-31-3 ]
Downstream synthetic route of [ 1201924-31-3 ]

[ 1201924-31-3 ] Synthesis Path-Upstream 1~4

1
[ 1201924-31-3 ]
[ 878207-92-2 ]

Reference： [1] Patent: WO2009/155156, 2009, A1,

2
[ 159727-88-5 ]
[ 1201924-31-3 ]

Reference： [1] Patent: WO2009/155156, 2009, A1, . Location in patent: Page/Page column 62-63
[2] Patent: WO2015/94912, 2015, A1, . Location in patent: Page/Page column 23-24
[3] Patent: WO2016/100156, 2016, A1, . Location in patent: Page/Page column 65; 66

3
[ 20970-75-6 ]
[ 1201924-31-3 ]

Reference： [1] Patent: WO2009/155156, 2009, A1,
[2] Patent: WO2015/94912, 2015, A1,

4
[ 1201924-31-3 ]
[ 1201924-32-4 ]

Reference： [1] Patent: WO2009/155156, 2009, A1, . Location in patent: Page/Page column 63

[ 1201924-31-3 ] Synthesis Path-Downstream 1~20

1
[ 20970-75-6 ]
[ 1201924-31-3 ]

Reference： [1]Patent: WO2009/155156,2009,A1
[2]Patent: WO2015/94912,2015,A1

2
[ 159727-88-5 ]
[ 1201924-31-3 ]

Yield	Reaction Conditions	Operation in experiment
		Step 2. 6-Chloro-3-methylpyridine-2-carbonitrile3-Methylpyridme-2-carbordtrile 1 -oxide (8.42 g, 62.8 mmol) was stirred in refluxing POCl3 (60 mL, 646 mmol) for 6 hours. The mixture was cooled to room temperature and slowly poured into ice- water. The resulting beige precipitate was collected by filtration to give the title compound.1H NMR (600 MHz, CDCl3): delta 7.62 (d, J- 8.4 Hz, 1 H), 7.43 (d, J- 8.4 Hz, 1 H), 2.53 (s, 3 H).
	With trichlorophosphate; In toluene; at 90.0℃; for 1.5h;	To a round bottom flask is added 3-methyl-l-oxo-pyridine-2- carbonitrile (16.2 g, 120.77 mmoles), toluene (8 mL), and phosphoryl chloride (16.83 mL; 181.2 mmoles). The mixture is stirred at 90 C for 90 minutes, cooled to RT, and added dropwise to aqueous 2M KH2PO4 (483 mL; 966 mmoles). The mixture is stirred 30 minutes, and the layers are separated. The organic layer is dried over MgS04, filtered, and concentrated to 6-chloro-3-methyl-pyridine-2-carbonitril: Mass spectrum (m/z): 153.0 (M+H)+. Phenylboronic acid (17.94 g, 144.9 mmoles), toluene (130 mL), sodium carbonate (190.2 g, 362.31 mmoles), bis(triphenylphosphine)palladium(II) chloride (856 mg; 1.21 mmoles) are added to this crude material. The mixture is stirred at 80C for 1 hour and cooled to RT. The layers are separated, and the organic layer is dried over MgS04, filtered, and concentrated. The material was purified by silica gel chromatography (400 g ISCO cartridge) using methylene chloride in hexanes from 20 to 100% to afford 3-methyl-6-phenyl-pyridine-2-carbonitrile (6.7 g, 28.6%). Mass spectrum (m/z): 195.1 (M+H)+.
	With trichlorophosphate; for 1h;Reflux;	A mixture of the product from Step 1 (1.2 g, 8.95 mmol) in POCl3 (29.7 g, 194 mmol) was stirred at reflux for 1 h. The mixture was cooled to RT, poured into 50 mL of water, and basified with saturated, aqueous NaHCC to pH 7-8, and extracted with EtOAc (100 mL). The organic phase was washed with brine (50 mL), dried over Na2SC>4, filtered, and concentrated in vacuo to give the title compound as a solid, which was used in the next step without further purification. LRMS m/z (M+H) 153.1 found, 153.0 required.

Reference： [1]Patent: WO2009/155156,2009,A1 .Location in patent: Page/Page column 62-63
[2]Patent: WO2015/94912,2015,A1 .Location in patent: Page/Page column 23-24
[3]Patent: WO2016/100156,2016,A1 .Location in patent: Page/Page column 65; 66

3
[ 1201924-31-3 ]
[ 878207-92-2 ]

Reference： [1]Patent: WO2009/155156,2009,A1

4
[ 1201924-31-3 ]
[ 1201924-32-4 ]

Yield	Reaction Conditions	Operation in experiment
		Step 3. 6-Chloro-3 -methylpyridine-2-carboxylic acid6-Chloro-3-methylrhoyridine-2-carbonitrile (2.95 g, 19.3 mmol) and Potassium hydroxide (3.25 g, 58 mmol) were stirred in refluxing water (60 mL) for 2 hours. The mixture was cooled to room temperature, 30 mL of 2 N HCl was added, followed by the addition of water. The resulting mixture was extracted with EtOAc (3x). The combined organic extracts were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo to give the title compound as a white solid.1H NMR (600 MHz, DMSO): delta 13.45 (br s, 1 H), 7.81 (d, J= 8.4 Hz5 1 H), 7.55 (d, J- 8.4 Hz, 1 H), 2.39 (s, 3 H).

Reference： [1]Patent: WO2009/155156,2009,A1 .Location in patent: Page/Page column 63

5
[ 1201924-31-3 ]
[ 1201924-34-6 ]

Reference： [1]Patent: WO2009/155156,2009,A1

6
[ 1201924-31-3 ]
[ 98-80-6 ]
3-methyl-6-phenyl-pyridine-2-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
6.7 g	With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In toluene; at 80.0℃; for 1h;	To a round bottom flask is added 3-methyl-l-oxo-pyridine-2- carbonitrile (16.2 g, 120.77 mmoles), toluene (8 mL), and phosphoryl chloride (16.83 mL; 181.2 mmoles). The mixture is stirred at 90 C for 90 minutes, cooled to RT, and added dropwise to aqueous 2M KH2PO4 (483 mL; 966 mmoles). The mixture is stirred 30 minutes, and the layers are separated. The organic layer is dried over MgS04, filtered, and concentrated to 6-chloro-3-methyl-pyridine-2-carbonitril: Mass spectrum (m/z): 153.0 (M+H)+. Phenylboronic acid (17.94 g, 144.9 mmoles), toluene (130 mL), sodium carbonate (190.2 g, 362.31 mmoles), bis(triphenylphosphine)palladium(II) chloride (856 mg; 1.21 mmoles) are added to this crude material. The mixture is stirred at 80C for 1 hour and cooled to RT. The layers are separated, and the organic layer is dried over MgS04, filtered, and concentrated. The material was purified by silica gel chromatography (400 g ISCO cartridge) using methylene chloride in hexanes from 20 to 100% to afford 3-methyl-6-phenyl-pyridine-2-carbonitrile (6.7 g, 28.6%). Mass spectrum (m/z): 195.1 (M+H)+.

Reference： [1]Patent: WO2015/94912,2015,A1 .Location in patent: Page/Page column 23-24

7
[ 1201924-31-3 ]
3-methyl-6-phenyl-pyridine-2-carboxylic acid [ No CAS ]

Reference： [1]Patent: WO2015/94912,2015,A1

8
[ 1201924-31-3 ]
methyl 2,4-dimethyl-3-[(3-methyl-6-phenyl-pyridine-2-carbonyl)amino]benzoate [ No CAS ]

Reference： [1]Patent: WO2015/94912,2015,A1
[2]Patent: WO2015/94912,2015,A1

9
[ 1201924-31-3 ]
2,4-dimethyl-3-[(3-methyl-6-phenyl-pyridine-2-carbonyl)amino]benzoic aicd [ No CAS ]

Reference： [1]Patent: WO2015/94912,2015,A1
[2]Patent: WO2015/94912,2015,A1

10
[ 1201924-31-3 ]
3-methyl-6-phenyl-pyridine-2-carbonyl chloride [ No CAS ]

Reference： [1]Patent: WO2015/94912,2015,A1

11
[ 1201924-31-3 ]
N-ethyl-N-(2-(6-(2-hydroxypropan-2-yl)-5-methylpyridin-2-yl)ethyl)-2-(2H-1,2,3-triazol-2-yl)benzamide [ No CAS ]

Reference： [1]Patent: WO2016/100156,2016,A1

12
[ 1201924-31-3 ]
6-(2-(ethylamino)ethyl)-3-methylpicolinonitrile [ No CAS ]

Reference： [1]Patent: WO2016/100156,2016,A1

13
[ 1201924-31-3 ]
N-(2-(6-cyano-5-methylpyridin-2-yl)ethyl)-N-ethyl-2-(2H-1,2,3-triazol-2-yl)benzamide [ No CAS ]

Reference： [1]Patent: WO2016/100156,2016,A1

14
[ 1201924-31-3 ]
N-(2-(6-acetyl-5-methylpyridin-2-yl)ethyl)-N-ethyl-2-(2H-1,2,3-triazol-2-yl)benzamide [ No CAS ]

Reference： [1]Patent: WO2016/100156,2016,A1

15
[ 1201924-31-3 ]
potassium vinyltrifluoroborate [ No CAS ]
3-methyl-6-vinylpicolinonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; at 90.0℃;Inert atmosphere;	To a stirred mixture of the product from Step 2 (200 mg, 1.31 mmol), Pd(Ph3P)4 (76 mg, 0.066 mmol), and Na2C03 (278 mg, 2.62 mmol) in toluene (4 mL), EtOH (2 mL), and water (1 mL) was added potassium vinyltrifluoroborate (263 mg, 1.97 mmol) under N2. The resulting mixture was stirred at 90C overnight. The mixture was cooled to RT, and then the organic layer was separated. The organic phase was washed with water (5 mL x 2), dried over Na2SC>4, filtered, and concentrated in vacuo. The residue was purified by prep-TLC (50% EtOAc in petroleum ether) to give the title compound as a oil. LRMS m/z (M+H) 145.1 found, 145.1 required.

Reference： [1]Patent: WO2016/100156,2016,A1 .Location in patent: Page/Page column 66

16
[ 1201924-31-3 ]
[ 84477-72-5 ]
6-(3,3-dimethylpiperazin-1-yl)-3-methylpyridine-2-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With caesium carbonate; In 1-methyl-pyrrolidin-2-one; at 100.0℃;	A mixture of <strong>[1201924-31-3]6-chloro-3-methyl-pyridine-2-carbonitrile</strong> (914 mg, 5.99 mmol), 2,2- dimethylpiperazine (1000 ilL, 7.30 mmol) and cesium carbonate (2.27 g, 6.97 mmol) in NMP (12 mL) is heated at 100C overnight. The reaction is cooled down to room temperature and water (120 mL) is added. The mixture is extracted with Et20 (3 x 50 mL). The combined organic phases are washed with water (60 mL) and brine (60 mL), dried over Na2SO4 and concentrated under reduced pressure. The crude material isused without further purification in the next step (1.082g, 69%). ESI-MS m/z calc. 230.15315, found 230.68 (M+1)+; Retention time: 1.03 minutes using Method L.

Reference： [1]Patent: WO2018/57588,2018,A1 .Location in patent: Paragraph 0253

17
[ 1201924-31-3 ]
[ 84477-72-5 ]
methyl 6-(3,3-dimethylpiperazin-1-yl)-3-methylpyridine-2-carboxylate hydrochloride [ No CAS ]

Reference： [1]Patent: WO2018/57588,2018,A1

18
[ 1201924-31-3 ]
[ 75-03-6 ]
6-chloro-5-ethyl-3-methylpicolinonitrile [ No CAS ]
6-chloro-4-ethyl-3-methylpicolinonitrile [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2018,vol. 83,p. 10933 - 10940

19
[ 75-30-9 ]
[ 1201924-31-3 ]
6-chloro-5-isopropyl-3-methylpyridine-2-carbonitrile [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2018,vol. 83,p. 10933 - 10940

20
[ 159727-88-5 ]
[ 1201924-31-3 ]
[ 886372-07-2 ]

Yield	Reaction Conditions	Operation in experiment
1: 30% 2: 68%	With trichlorophosphate at 0 - 80℃; for 6h;	4-chloro-3-methyl-picolinonitrile (14) Phosphorus oxychloride (50 mL) was added to a three-neck round-bottom flask and cooled to 0 °C, following slowly addition of 15 (8 g, 0.06 mol). The mixture was stirred at ice bath for 2 hours before the temperature was increased to 80 °C and further stirred for another 4 hours. The resulting mixture was cooled to room temperature and the reaction was quenched by pouring the mixture to a beaker with 200 mL of ice water. The mixture was cooled to room temperature and extracted by ethyl acetate (100 mL) for three times. The combined organic layers were washed by saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was removed under vacuum to afford a crude product. The crude product was purified by column chromatography (silica gel) eluting with petroleum ether / ethyl acetate = 20 / 1 to afford a white pure product. Yield, 3.0 g, 30 %. 20 %. 1H NMR (600 MHz, CDCl3) δ 8.45 (d, J = 5.1 Hz, 1H), 7.53 (d, J = 5.2 Hz, 1H), 2.63 (s, 3H). 13C NMR (150 MHz, CDCl3) δ 149.26, 145.90, 137.59, 135.66, 127.76, 116.16, 17.08. MS (ESI) m/z ([M+H]+): 152.9. MP: 146-148 °C; Rf = 0.3 (5% EtOAc/petroleum ether). The main side product is 6-chloro-3-methyl-picolinonitrile, white solid, Yield, 6.8 g, 68 %. 1H NMR (CDCl3) δ 7.65 (d, J = 8.3 Hz, 1H), 7.45 (d, J = 8.3 Hz, 1H), 2.56 (s, 3H). 13C NMR (CDCl3) δ 149.96, 141.03, 137.78, 133.50, 128.12, 115.38, 18.29. MS (ESI) m/z ([M+H]+): 152.9. MP: 74-76 °C; Rf = 0.4 (5 % EtOAc/petroleum ether). The 1H NMR and 13C NMR were shown in supplement information-Figure- S7, S8.

Reference： [1]Bao, Xuefei; Chang, Yan; Chen, Guoliang; He, Xiaoyan; Liu, Zi'ao; Lu, Xiuhong [Tetrahedron Letters, 2020]

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P502	Refer to manufacturer/supplier for information on recovery/recycling

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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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. 1201924-31-3 ] {[proInfo.proName]}

Quality Control of [ 1201924-31-3 ]

Related Doc. of [ 1201924-31-3 ]

Product Details of [ 1201924-31-3 ]

Calculated chemistry of [ 1201924-31-3 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 1201924-31-3 ]

Application In Synthesis of [ 1201924-31-3 ]

[ 1201924-31-3 ] Synthesis Path-Upstream 1~4

[ 1201924-31-3 ] Synthesis Path-Downstream 1~20

Related Functional Groups of [ 1201924-31-3 ]

Chlorides

Nitriles

Related Parent Nucleus of [ 1201924-31-3 ]

Pyridines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 1201924-31-3 ]

Related Parent Nucleus of
[ 1201924-31-3 ]