2-Chloro-6-aminopyrazine Chemical Properties

Melting point:

150-152°C

Boiling point:

282.8±35.0 °C(Predicted)

Density 

1.437±0.06 g/cm3(Predicted)

storage temp. 

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

solubility 

Soluble in dimethyl sulfoxide and methanol.

form 

Solid

pka

0.89±0.10(Predicted)

color 

Purple

InChI

InChI=1S/C4H4ClN3/c5-3-1-7-2-4(6)8-3/h1-2H,(H2,6,8)

InChIKey

JTPXVCKCLBROOJ-UHFFFAOYSA-N

SMILES

C1(N)=NC(Cl)=CN=C1

LogP

0.950

CAS DataBase Reference

33332-28-4(CAS DataBase Reference)

EPA Substance Registry System

2-Amino-6-chloropyrazine (33332-28-4)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-41-22

Safety Statements 

26-36/37/39-60-37

TSCA 

Yes

HazardClass 

IRRITANT

HS Code 

29339900

2-Chloro-6-aminopyrazine Usage And Synthesis

Chemical Properties

2-Chloro-6-aminopyrazine is Purple Solid

Uses

2-Chloro-6-aminopyrazine is a disubstituted pyrazine used in the preparation of A2B adenosine receptor antagonists and other biologically active compounds.

Uses

2-Amino-6-chloropyrazine is used in the preparation of A2B adenosine receptor antagonists and other biologically active compounds.

Synthesis

General procedure for the synthesis of 2-amino-6-chloropyrazine from 2,6-dichloropyrazine: 2,6-dichloropyrazine (10.0 g, 67.1 mmol) and ammonia (100 mL) were sequentially added to a hydrothermal reactor and reacted at 100 °C for 5 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and the solid product was collected by filtration. The filter cake was pulped with hexane (16 mL) to give a final white solid of 8.2 g of 2-amino-6-chloropyrazine in 95.0% yield.

References

[1] Patent: CN107857737, 2018, A. Location in patent: Paragraph 0011-0013; 0021-0023; 0030-0032; 0040-0042; 0049
[2] Journal of Medicinal Chemistry, 2011, vol. 54, # 24, p. 8328 - 8342
[3] Patent: WO2013/68755, 2013, A1. Location in patent: Page/Page column 67, 68
[4] Patent: WO2017/5786, 2017, A1. Location in patent: Page/Page column 23; 24
[5] Tetrahedron, 1984, vol. 40, # 24, p. 5081 - 5088

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