Methyl 5-chloropyrazine-2-carboxylate Chemical Properties

Melting point:

89-90 °C(Solv: ligroine (8032-32-4))

Boiling point:

242.8±35.0 °C(Predicted)

Density 

1.372±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

Solid

pka

-4.54±0.10(Predicted)

Appearance

Light brown to gray Solid

InChI

InChI=1S/C6H5ClN2O2/c1-11-6(10)4-2-9-5(7)3-8-4/h2-3H,1H3

InChIKey

CVVMLRFXZPKILB-UHFFFAOYSA-N

SMILES

C1(C(OC)=O)=NC=C(Cl)N=C1

CAS DataBase Reference

33332-25-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2933998090

Methyl 5-chloropyrazine-2-carboxylate Usage And Synthesis

Chemical Properties

Methyl 5-chloropyrazine-2-carboxylate has a melting point of 89-90°C, a boiling point of 242.8±35.0°C (Predicted), a density of 1.372±0.06 g/cm3 (Predicted), and an acidity factor (pKa) of -4.54±0.10 (Predicted).

Uses

Methyl 5-chloropyrazine-2-carboxylate can be used as an intermediate in many pharmaceuticals and pesticides. It can also be used as organic reaction reagent or other chemical products manufacturing.

Synthesis

General procedure for the synthesis of methyl 5-chloropyrazine-2-carboxylate from methyl 5-hydroxypyrazine-2-carboxylate: Methyl 5-hydroxypyrazine-2-carboxylate (673 mg, 4.37 mmol) was dissolved in phosphorus trichloride (6.1 mL), and a few drops of N,N-dimethylformamide were added as catalyst. The reaction mixture was heated to reflux for 2 h under nitrogen protection. After completion of the reaction, the reaction solution was slowly poured into ice water and extracted three times with chloroform (30 mL). The organic layers were combined and washed sequentially with saturated aqueous sodium bicarbonate and saturated saline (100 mL each). The organic layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure to remove the solvent to give methyl 5-chloropyrazine-2-carboxylate (611 mg, 81% yield) as a gray solid. The structure of the product was confirmed by 1H-NMR (CDCl3, 400 MHz): δ 4.05 (3H, s), 8.71 (1H, d, J = 1.6 Hz), 9.10 (1H, d, J = 1.2 Hz).

References

[1] Patent: EP2239253, 2010, A1. Location in patent: Page/Page column 96
[2] Patent: WO2013/14567, 2013, A1. Location in patent: Page/Page column 81
[3] Patent: EP1452525, 2004, A1. Location in patent: Page 15-16

Methyl 5-chloropyrazine-2-carboxylate(33332-25-1)Related Product Information

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