5-amino-1H-imidazole-4-carboxamide hydrochloride

• ChemBase ID: 78329
• Molecular Formular: C4H7ClN4O
• Molecular Mass: 162.57758
• Monoisotopic Mass: 162.03083854
• SMILES: [nH]1c(c(C(=O)N)nc1)N.Cl
• Canonical SMILES: NC(=O)c1nc[nH]c1N.Cl
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-amino-1H-imidazole-4-carboxamide hydrochloride; 4-amino-1H-imidazole-5-carboxamide hydrochloride
• IUPAC Traditional name: 5-aminoimidazole-4-carboxamide hydrochloride; 4-aminoimidazole-5-carboxamide hydrochloride; 4-amino-5-imidazolecarboxamide hydrochloride
• Synonyms: 4-Amino-5-imidazolecarboxamide hydrochloride; 5-Amino-1H-imidazole-4-carboxamide hydrochloride; 5-Amino-1H-imidazole-4-carboxamide hydrochloride 98%; 5-Amino-4-imidazolecarboxamide hydrochloride; 4-AMINO-5-CARBOXAMIDO IMIDAZOLE HYDROCHLORIDE; 4(5)-amino-5(4)-imidazolecarboxamide hydrochloride; AICA; 5(4)-AMINOIMIDAZOLE-4(5)-CARBOXAMIDE HYDROCHLORIDE; 4-Aminoimidazole-5-carboxamide hydrochloride; 4-amino-5-imidazolecarboxamide hydrochloride; 4-amino-1H-imidazole-5-carboxamide hydrochloride; 4-氨基-5-咪唑甲酰胺 盐酸盐; 5-氨基-4-甲酰胺咪唑 盐酸盐; 4-氨基咪唑-5-甲酰胺盐酸盐

Database IDs

• CAS Number: 72-40-2
• EC Number: 200-778-3
• MDL Number: MFCD00799200; MFCD00012704
• Beilstein Number: 3701645
• PubChem SID: 24891305; 162043098; 24850109; 24846032
• PubChem CID: 66146

CALCULATED PROPERTIES

• Acid pKa: 12.742147
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): -1.1360245
• LogD (pH = 7.4): -0.96191853
• Log P: -0.9590512
• Molar Refractivity: 32.9826 cm^3
• Polarizability: 11.236273 Å^3
• Polar Surface Area: 97.79 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: off-white to light green crystalline
• Melting Point: 250-252 °C (dec.)(lit.); 250-252°C; 257 - 259°C; ca 270°C dec.
• Hydrophobicity(logP): -0.555

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• Storage Warning: Hygroscopic; Irritant
• RTECS: NI3911000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: R:22
• Safety Statements: S:36/37/39
• TSCA Listed: 是
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥99.0% (AT); 95%; 98%
• Grade: purum
• Empirical Formula (Hill Notation): C4H6N4O · HCl

DETAILS

MP Biomedicals - 05207512

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02100629

Hydrochloride
Crystalline
Important starting material for purine synthesis.

Sigma Aldrich - 164968

Packaging
25 g in poly bottle
5 g in glass bottle
Application
Reactant for synthesis of heterocyclic compounds such as purines1,2 and pyrimidines.3

Sigma Aldrich - 08220

Other Notes
Base of the nucleotide ZTP, isolated from bacterial cells1,2

REFERENCES

• Starting material for synthesis of the antitumour agent temozolomide. A synthetic pathway employing Ethyl isocyanatoacetate, L10609 avoids the use of the highly toxic methyl isocyanate: J. Chem. Soc., Perkin 1, 2783 (1995).