ChemicalBook--->CAS DataBase List--->18368-76-8

18368-76-8

18368-76-8 Structure

18368-76-8 Structure
IdentificationMore
[Name]

2-Chloro-3-picoline
[CAS]

18368-76-8
[Synonyms]

2-CHLORO-3-METHYLPYRIDINE
2-CHLORO-3-PICOLINE
2-CHLORO-3-METHYLPYRIDINE 98%
2-CHLORO-3-METHYLPYRRIDINE
2-CHLORO-3-PICOLINE 2-CHLORO-3-METHYLPYRIDINE
2-CHLORO-3-METHYLPYRIDINE (2-CHLORO-3-PICOLINE)
2-Chloro-3-methylpyridine, 98+%
2-Choro-3-methypyridine
[EINECS(EC#)]

242-242-1
[Molecular Formula]

C6H6ClN
[MDL Number]

MFCD00234177
[Molecular Weight]

127.57
[MOL File]

18368-76-8.mol
Chemical PropertiesBack Directory
[Appearance]

colorless to light yellow liquid
[Melting point ]

193 °C
[Boiling point ]

192-193 °C/751 mmHg (lit.)
[density ]

1.17 g/mL at 25 °C(lit.)
[refractive index ]

n20/D 1.533(lit.)
[Fp ]

175 °F
[storage temp. ]

Inert atmosphere,Room Temperature
[form ]

Liquid
[pka]

0.75±0.10(Predicted)
[color ]

Colorless to light yellow
[Specific Gravity]

1.170
[BRN ]

107895
[InChI]

InChI=1S/C6H6ClN/c1-5-3-2-4-8-6(5)7/h2-4H,1H3
[InChIKey]

RKVUCIFREKHYTL-UHFFFAOYSA-N
[SMILES]

C1(Cl)=NC=CC=C1C
[CAS DataBase Reference]

18368-76-8(CAS DataBase Reference)
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)Skull and Crossbones (GHS06)
GHS07,GHS06
[Signal word ]

Warning
[Hazard statements ]

H227-H302+H312+H332-H302-H312-H331-H315-H319-H335
[Precautionary statements ]

P210e-P405-P501a-P210-P261-P264-P270-P271-P280-P301+P312+P330-P302+P352+P312+P362+P364-P304+P340+P312-P305+P351+P338+P337+P313-P403+P235-P501-P305+P351+P338
[Hazard Codes ]

Xi,Xn
[Risk Statements ]

R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
[Safety Statements ]

S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
[RIDADR ]

2810
[WGK Germany ]

3
[HazardClass ]

6.1
[PackingGroup ]

III
[HS Code ]

29333990
Raw materials And Preparation ProductsBack Directory
[Raw materials]

3-Methylpyridine-2-carboxylic acid-->Di-tert-butyl peroxide-->Sodium hydroxide-->Tetrabutyl ammonium chloride-->Acetonitrile
[Preparation Products]

2-Chloro-5-methylpyridine-->2-Amino-4-methoxypyridine-3-carboxylic acid-->2-Chloro-4-methoxy-3-methylpyridine-->2-Chloro-3-methyl-4-methoxypyridine N-oxide-->2-Chloro-3-methyl-4-nitropyridine N-oxide-->2-Chloronicotinic acid-->1-(3-Methylpyridin-2-yl)piperazine-->2-Chloro-3,6-dimethylpyridine-->(3-Methyl-pyridin-2-yl)-hydrazine-->2-Bromo-3-(chloromethyl)pyridine
Hazard InformationBack Directory
[Description]

2-Chloro-3-methylpyridine is an intermediate for many medicines and pesticides, such as fluazifop, nicosulfuron, and fluazifop. Moreover, with the gradual promotion of these new high-efficiency and low-toxic heterocyclic pesticides, 2-chloro-3-methylpyridine is increasing. The industrial method for preparing 2-chloro-3-methylpyridine is to obtain it by site-specific chlorination of 3-methylpyridine. First, 3-methylpyridine is epoxidized and then chlorinated. The main chlorinated 3-methylpyridine is a mixture of 2-chloro-3-methylpyridine and 2-chloro-5-methylpyridine, of which 2-chloro-3-methylpyridine accounts for 20% (mass).
[Chemical Properties]

colorless to light yellow liquid
[Uses]

2-Chloro-3-methylpyridine is an active ingredient and a major constituent of imidaclopide, a systemic insecticide that acts as insect neurotoxin and belongs to a class of chemical called the neonicotinoids.
[Synthesis]

3-Methylpyridine-2-carboxylic acid

4021-07-2

2-Chloro-3-methylpyridine

18368-76-8

General procedure for the synthesis of 2-chloro-3-methylpyridine from 3-methyl-2-pyridinecarboxylic acid: 3-methylpyridine-2-carboxylic acid (56.7 mg, 0.3 mmol), sodium hydroxide (16.0 mg, 0.15 mmol), tetrabutylammonium chloride (TBAC, 26.3 mg, 0.45 mmol) and di-tert-butyl peroxide (DTBP. 165 μL, 0.9 mmol) were placed in a 25 mL Schlenk reaction flask. Subsequently, 1 mL of acetonitrile (CH3CN) was added as a solvent and the reaction mixture was placed in an oil bath at 50 °C for 20 h. The reaction was carried out at a pressure of 1.5 mL. After completion of the reaction, the solvent was removed by distillation under reduced pressure. The crude product was purified by silica gel column chromatography using petroleum ether/ethyl acetate as eluent to give 2-chloro-3-methylpyridine in 70% yield.

[References]

[1] Patent: CN108586334, 2018, A. Location in patent: Paragraph 0048-0050
Spectrum DetailBack Directory
[Spectrum Detail]

2-Chloro-3-picoline(18368-76-8)MS
2-Chloro-3-picoline(18368-76-8)1HNMR
2-Chloro-3-picoline(18368-76-8)13CNMR
2-Chloro-3-picoline(18368-76-8)IR1
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

2-Chloro-3-picoline, 98%(18368-76-8)
[Alfa Aesar]

2-Chloro-3-methylpyridine, 98+%(18368-76-8)
[Sigma Aldrich]

18368-76-8(sigmaaldrich)
[TCI AMERICA]

2-Chloro-3-picoline,>97.0%(GC)(18368-76-8)
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