4-Amino-5-imidazolecarboxamide hydrochloride Chemical Properties

Melting point:

250-252 °C (dec.)(lit.)

storage temp. 

2-8°C

solubility 

water: soluble50mg/mL, clear, light yellow

form 

Crystals or Crystalline Powder

color 

White

Water Solubility 

SOLUBLE

Sensitive 

Hygroscopic

BRN 

3701645

Stability:

Hygroscopic

InChI

InChI=1S/C4H6N4O.ClH/c5-3-2(4(6)9)7-1-8-3;/h1H,5H2,(H2,6,9)(H,7,8);1H

InChIKey

MXCUYSMIELHIQL-UHFFFAOYSA-N

SMILES

C1(N=CNC=1N)C(=O)N.Cl

CAS DataBase Reference

72-40-2(CAS DataBase Reference)

NIST Chemistry Reference

Imidazole-4(5)-carboxamide, 5-(4)-amino-, hydrochloride(72-40-2)

EPA Substance Registry System

1H-Imidazole-4-carboxamide, 5-amino-, monohydrochloride (72-40-2)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

20/21/22-36/37/38

Safety Statements 

22-24/25-36-26

WGK Germany 

3

RTECS 

NI3911000

Hazard Note 

Irritant

TSCA 

Yes

HS Code 

29332990

MSDS

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

4-Amino-5-imidazolecarboxamide hydrochloride Usage And Synthesis

Chemical Properties

very slightly beige fine powder

Uses

5-Amino-4-imidazolecarboxamide hydrochloride was used in the synthesis of heterocyclic compounds such as guanine, purines and pyrimidines.

General Description

Corrosion inhibition and adsorption characteristics of 5-amino-4-imidazolecarboxamide hydrochloride on aluminum in 1M HCl has been investigated.

Synthesis

47 g of sodium nitrite was dissolved in 1.2 liters of water; The solution was cooled to 0° C. 100 g of 5-aminoimidazole-4 carboxamide was dissolved in a solution of hydrochloric acid (80 ml of 36% HCL in 720 ml water) with stirring. The resultant 5-aminoimidazole-4 carboxamide hydrochloride solution was added slowly, drop-wise, over 20-30 minutes at 0-5° C. After the addition was completed, the reaction mixture was stirred for 10 minutes and filtered. The solid obtained was suspended in 400 ml DM water and stirred for 15 minutes. The suspension was filtered and suction-dried for 15 minutes. The obtained solid was suspended in 500 ml of THF and stirred for 15 minutes. The suspension was filtered and suction-dried for 15 minutes. Finally, the solid was dried at 45° C. to afford 4-Amino-5-imidazolecarboxamide hydrochloride.

Purification Methods

Recrystallise the hydrochloride from EtOH. [Kuroda & Hakko JEst(1) Est(2)Heterocycl Chem 30 593 1993, Alhede et al. J Org Chem 56 2139 1991, Cheru et al. Heterocycles 24 1133 1992, Beilstein 25 II 221, 25 III/IV 4329.]

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