PYRAZINE-2-CARBOXAMIDINE HYDROCHLORIDE

PYRAZINE-2-CARBOXAMIDINE HYDROCHLORIDE Property

storage temp. 

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

form 

solid

color 

White

CAS DataBase Reference

138588-41-7(CAS DataBase Reference)

Safety

Hazard Codes 

Xi,Xn

Risk Statements 

22

HazardClass 

IRRITANT

HS Code 

2933998090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P321Specific treatment (see … on this label).

P330Rinse mouth.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P501Dispose of contents/container to..…

PYRAZINE-2-CARBOXAMIDINE HYDROCHLORIDE Chemical Properties,Usage,Production

Synthesis

The general procedure for the synthesis of 2-pyrazinamidine hydrochloride from 2-cyanopyrazine was as follows: 2-cyanopyrazine (1.00 kg, 9.53 mol) was slowly added to a solution of sodium methanol (NaOCH3, 51.4 g, 0.952 mol) in methanol (3800 mL) at room temperature. The reaction mixture was heated to 30 °C and stirred for 6 hours. Upon completion of the reaction, the mixture was cooled to 25 °C, followed by the addition of ammonium chloride (NH4Cl, 572 g, 10.5 mol). Stirring of the reaction mixture was continued for 22 hours. At the end of the reaction, methyl tert-butyl ether (4000 mL) was added and stirred for 15 minutes to promote solid formation. The solid product was collected by filtration and washed with methyl tert-butyl ether (2 x 1000 mL). Finally, the product was dried at 40 °C, 0-10 mmHg for 17 h to give the white solid product 2-pyrazinamidine hydrochloride (1435 g) in 95% yield and 95% purity by HPLC.1H NMR (DMSO-D6) data were as follows: δ 9.7 (broad single peak, 3H), 9.49 (double peak, 1H, J=1.5Hz), 9.04 (multiple peaks, 1H), 8.93 (multiple peaks, 1H), 9.04 (multiple peaks, 1H), 8.93 (multiple peaks 1H), 8.93 (triple peak, 1H, J=1.5Hz).

References

[1] Patent: US2006/281760, 2006, A1. Location in patent: Page/Page column 5; 8
[2] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 1, p. 111 - 118
[3] Patent: US2005/75357, 2005, A1. Location in patent: Page/Page column 35
[4] Patent: WO2005/79798, 2005, A1. Location in patent: Page/Page column 150
[5] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 1, p. 299 - 301