2-Amino-3-chloropyrazine Chemical Properties

Melting point:

167-171°C

Boiling point:

248.1±35.0 °C(Predicted)

Density 

1.437±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

powder to crystal

pka

2.37±0.10(Predicted)

color 

White to Light yellow to Dark green

Water Solubility 

Slightly soluble in water.

InChI

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

InChIKey

AEVSSZHXGJAPIE-UHFFFAOYSA-N

SMILES

C1(N)=NC=CN=C1Cl

CAS DataBase Reference

6863-73-6

Safety Information

Risk Statements 

36/37/38

Safety Statements 

26-37

HazardClass 

IRRITANT

HS Code 

29339900

2-Amino-3-chloropyrazine Usage And Synthesis

Uses

It is employed in the synthesis and tuberculostatic activity of N-pyrazinylthiourea.

Synthesis

General procedure for the synthesis of 2-amino-3-chloropyrazine from 2,3-dichloropyrazine: 2,3-dichloropyrazine (3.5 g, 0.023 mol) was suspended in a mixture of 25% ammonia (20 mL) and tetrahydrofuran (THF, 20 mL) in an autoclave reactor and heated to react for 18 h at 100 °C. The reaction was completed by cooling to room temperature. After completion of the reaction, it was cooled to room temperature and the reaction mixture was concentrated under reduced pressure to a minimum volume. The residue was ground with distilled water (15 mL) and after filtration, the solid product was dried to give 2-amino-3-chloropyrazine as a light yellow crystalline solid (2.75 g, 90% yield). Mass spectrum (electrospray positive ionization mode, ES+) m/z: 130.1. 1H NMR (400 MHz, CDCl3): δ 7.94 (d, J=2.53 Hz, 1H), 7.72 (d, J=2.53 Hz, 1H), 4.90-5.12 (broad single peak, 2H).

References

[1] Patent: US2012/59162, 2012, A1. Location in patent: Page/Page column 38-39
[2] Journal of Medicinal Chemistry, 2014, vol. 57, # 10, p. 4196 - 4212
[3] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 15, p. 3454 - 3459
[4] Patent: US2014/364414, 2014, A1. Location in patent: Paragraph 0438-0440
[5] Patent: WO2010/69684, 2010, A1. Location in patent: Page/Page column 96

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