2-Chloro-3-methylpyridine Chemical Properties

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.)

Flash point:

175 °F

storage temp. 

Inert atmosphere,Room Temperature

pka

0.75±0.10(Predicted)

form 

Liquid

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 Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-20/21/22

Safety Statements 

26-36-36/37/39

RIDADR 

2810

WGK Germany 

3

HazardClass 

6.1

PackingGroup 

III

HS Code 

29333990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2-Chloro-3-methylpyridine Usage And Synthesis

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.

Application

2-Chloro-3-methylpyridine can be used as an intermediate for Lumacaftor. Lumacaftor is a drug used to treat certain types of cystic fibrosis, particularly by assisting in the transport of CFTR protein to the cell membrane surface, thereby addressing respiratory issues associated with the disease.

Synthesis

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

2-Chloro-3-methylpyridine(18368-76-8)Related Product Information

• Azamethiphos
• 2,6-Lutidine
• 5-Amino-2-methylpyridine
• 4-Methylpyridine
• 2,5-Dimethylpyridine
• 2-Chloro-3-nitropyridine
• 2-(Chloromethyl)pyridine
• 2-Chloro-3-cyano-4,6-dimethylpyridine
• PYRIDINITRIL
• ETHYL 2-CHLORO-3-CYANO-6-METHYLISONICOTINATE
• 2-Chloro-3-(trifluoromethyl)pyridine
• 2-CHLORO-4,6-DIMETHYLNICOTINAMIDE
• 2-Chloro-3-cyanopyridine
• 2,6-Dichloro-4-methylnicotinonitrile
• 2-Chloro-5-chloromethylpyridine
• 2-Chloronicotinic acid
• 2-Chloronicotinamide
• Difluorochloromethane