2-CHLORO-3-METHYLPYRAZINE Chemical Properties

Boiling point:

80 °C(Press: 27 Torr)

Density 

1.234g/ml

refractive index 

1.5283

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

-0.31±0.10(Predicted)

form 

Liquid

color 

Colorless

InChI

InChI=1S/C5H5ClN2/c1-4-5(6)8-3-2-7-4/h2-3H,1H3

InChIKey

WZHWPZQQPWKEAV-UHFFFAOYSA-N

SMILES

C1(Cl)=NC=CN=C1C

LogP

1.058 (est)

CAS DataBase Reference

95-58-9(CAS DataBase Reference)

EPA Substance Registry System

Pyrazine, 2-chloro-3-methyl- (95-58-9)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-37/38-41

Safety Statements 

26-39

TSCA 

Yes

HS Code 

2933119000

2-CHLORO-3-METHYLPYRAZINE Usage And Synthesis

Uses

2-Chloro-3-methylpyrazine is a pyrazine compound in which the chlorine atom in the structure can be replaced for the preparation of other medicinal chemicals. It is used in the preparation of macrocyclic urea kinase inhibitors.

Synthesis

(i) Chlorine gas was passed into carbon tetrachloride (67 mL) at a constant flow rate for 30 minutes. Subsequently, the resulting yellow solution was slowly added dropwise to a solution of carbon tetrachloride (125 mL) containing pyridine (4.8 mL) and 2-methylpyrazine (5 g) over a period of 30 minutes while stirring was maintained. Upon completion of the reaction, the reaction system was purged with nitrogen to remove residual chlorine gas, followed by removal of volatile solvents by rotary evaporation. The resulting brown oily crude product was purified by silica gel column chromatography using dichloromethane as eluent to give 2-chloro-3-methylpyrazine as a final brown oil (3.62 g, 53% yield). The structure of the product was confirmed by 1H NMR (d6-DMSO): δ 6.59 (s, 2H), 7.67 (d, 1H), 7.94 (d, 1H); the mass spectrum (+ve CI) showed the molecular ion peak m/z 129 ([M + H]+).

References

[1] Patent: US5861401, 1999, A
[2] Patent: CN107954913, 2018, A. Location in patent: Paragraph 0021

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