2-chloro-5-nitro-1H-imidazole

• ChemBase ID: 37047
• Molecular Formular: C3H2ClN3O2
• Molecular Mass: 147.51988
• Monoisotopic Mass: 146.983554
• SMILES: [nH]1c(nc(c1)[N+](=O)[O-])Cl
• Canonical SMILES: [O-][N+](=O)c1c[nH]c(n1)Cl
• InChI: InChI=1S/C3H2ClN3O2/c4-3-5-1-2(6-3)7(8)9/h1H,(H,5,6)
• InChIKey: BOJZBRDIZUHTCE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-chloro-5-nitro-1H-imidazole; 2-chloro-4-nitro-1H-imidazole
• IUPAC Traditional name: 2-chloro-4-nitro-3H-imidazole; 2-chloro-4-nitro-1H-imidazole
• Synonyms: 2-Chloro-5-nitroimidazole; 2-Chloro-5-nitro-1H-imidazole; 2-Chloro-4(5)-nitroimidazole; 2-Chloro-4-nitro-1H-imidazole; 2-Chloro-4-nitroimidazole; P21; 2-Chloro-4-nitroimidazole; 2-Chloro-4-nitro-1H-imidazole

Database IDs

• CAS Number: 57531-37-0
• MDL Number: MFCD03419295
• PubChem SID: 161000354
• PubChem CID: 42409

CALCULATED PROPERTIES

• Acid pKa: 8.108331
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.3022028
• LogD (pH = 7.4): 1.2287484
• Log P: 1.3032318
• Molar Refractivity: 30.6727 cm^3
• Polarizability: 11.273409 Å^3
• Polar Surface Area: 71.82 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 214-216°C

Safety Information

• Storage Warning: IRRITANT; Irritant
• TSCA Listed: false

Product Information

• Purity: 97%; 98%

DETAILS

Toronto Research Chemicals - C373935

4-Nitroimidazole derivative with poetenial use as radiosensitizers of hypoxic cells. It is used in the preparation of antitubercular nitroimidazoles.

REFERENCES

• Widel, M. et al.: Neoplasma, 3, 241 (1987)
• Kim, P. et al.: J. Med. Chem., 52, 1317 (1987)