3-Aminopyrazine-2-carboxylic acid Chemical Properties

Melting point:

205-210 °C (dec.) (lit.)

Boiling point:

255.04°C (rough estimate)

Density 

1.4551 (rough estimate)

refractive index 

1.5900 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

DMSO (Sparingly) , Methanol (Slightly)

pka

3.65±0.10(Predicted)

form 

Crystalline Powder

color 

Yellow-greenish

BRN 

124835

InChI

InChI=1S/C5H5N3O2/c6-4-3(5(9)10)7-1-2-8-4/h1-2H,(H2,6,8)(H,9,10)

InChIKey

ZAGZIOYVEIDDJA-UHFFFAOYSA-N

SMILES

C1(C(O)=O)=NC=CN=C1N

LogP

-3.1 at 20℃ and pH7

Surface tension

73.6mN/m at 1g/L and 20℃

CAS DataBase Reference

5424-01-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29339990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

3-Aminopyrazine-2-carboxylic acid Usage And Synthesis

Chemical Properties

Pale Brown Crystalline Solid

Uses

Antidiabetic

Synthesis

General procedure for the synthesis of 3-aminopyrazine-2-carboxylic acid from methyl 3-aminopyrazine-2-carboxylate: Methyl 3-aminopyrazine-2-carboxylate (2.08 g, 13.6 mmol) was suspended in methanol (40 mL) under nitrogen protection, and treated with 1N aqueous sodium hydroxide (30 mL). The reaction mixture was warmed up to room temperature and stirred for 50 min. Subsequently, methanol (about 45 mL) was partially evaporated under reduced pressure. The resulting mixture was cooled in an ice water bath and 1N aqueous hydrochloric acid solution (70 mL) was slowly added. Initially the mixture appeared as a solution and gradually a precipitate was generated with further addition of acid. The solid product was collected by filtration, washed with water (3 x 10 mL) and finally dried under vacuum to give 1.48 g of the target product 3-aminopyrazine-2-carboxylic acid.

References

[1] Journal of Medicinal Chemistry, 2011, vol. 54, # 7, p. 2320 - 2330
[2] Patent: WO2013/169907, 2013, A1. Location in patent: Page/Page column 44

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