METHYL 2-CHLORONICOTINATE Chemical Properties

Boiling point:

150 °C/1 mmHg

Density 

1.314 g/mL at 25 °C

refractive index 

n 20/D 1.537

Flash point:

110 °C

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

Liquid

pka

-1.39±0.10(Predicted)

color 

Colorless

CAS DataBase Reference

40134-18-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36

Safety Statements 

26

WGK Germany 

3

Hazard Note 

Irritant/Keep Cold

HS Code 

2933399990

METHYL 2-CHLORONICOTINATE Usage And Synthesis

Description

Methyl 2-chloronicotinate is used in proteomics studies.

Synthesis

(1) Preparation of methyl 2-chloronicotinate: 15.0 g (95.2 mmol) of 2-chloronicotinate was dissolved in 150 mL of dichloromethane and 8.37 mL (94.5 mmol) of oxalyl chloride was added slowly and dropwise. Subsequently, N,N-dimethylformamide was added dropwise to the mixture and the reaction mixture was stirred at room temperature for 3 hours. Upon completion of the reaction, 40.1 mL (286 mmol) of triethylamine and 37 mL (914 mmol) of methanol were added dropwise to the reaction mixture under ice-bath cooling conditions and stirring was continued for 30 minutes under ice-bath cooling. The reaction mixture was concentrated under reduced pressure and neutralized by adding aqueous sodium bicarbonate to the residue. The aqueous phase was extracted with ether, the organic phases were combined, washed with water, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by column chromatography (eluent: ethyl acetate/hexane=1:4) to afford 13.9 g of the target product methyl 2-chloronicotinate as a pale yellow liquid in 86% yield.1H-NMR (CDCl3/TMS, δ ppm): 3.97 (3H, s), 7.33 (1H, dd), 8.17 (1H, dd), 8.53 (1H, dd ).

References

[1] Patent: CN105061399, 2017, B. Location in patent: Paragraph 0010; 0029; 0030
[2] Patent: US2011/287937, 2011, A1. Location in patent: Page/Page column 72-73
[3] Patent: WO2007/71900, 2007, A1. Location in patent: Page/Page column 94
[4] Yakugaku Zasshi, 1952, vol. 72, p. 1336,1338
[5] Chem.Abstr., 1953, p. 4336

METHYL 2-CHLORONICOTINATE(40134-18-7)Related Product Information

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