methyl 1H-1,3-benzodiazole-6-carboxylate

• ChemBase ID: 69941
• Molecular Formular: C9H8N2O2
• Molecular Mass: 176.17202
• Monoisotopic Mass: 176.05857751
• SMILES: c1nc2c([nH]1)ccc(c2)C(=O)OC
• Canonical SMILES: COC(=O)c1ccc2c(c1)nc[nH]2
• InChI: InChI=1S/C9H8N2O2/c1-13-9(12)6-2-3-7-8(4-6)11-5-10-7/h2-5H,1H3,(H,10,11)
• InChIKey: WJHHIVYNOVTVGY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 1H-1,3-benzodiazole-6-carboxylate; methyl 1H-1,3-benzodiazole-5-carboxylate
• IUPAC Traditional name: methyl 3H-1,3-benzodiazole-5-carboxylate; methyl 1H-1,3-benzodiazole-5-carboxylate
• Synonyms: 1H-Benzimidazole-6-carboxylic Acid Methyl Ester; 5-Benzimidazolecarboxylic Acid Methyl Ester; 5-(Methoxycarbonyl)benzimidazole; Methyl 5-Benzimidazolecarboxylate; Methyl 1H-Benzimidazole-5-carboxylate; 1H-Benzimidazole-5-carboxylic Acid Methyl Ester; methyl 1H-1,3-benzodiazole-5-carboxylate; methyl 1H-benzo[d]imidazole-5-carboxylate; Methyl benzimidazole-5-carboxylate; Methyl 1H-benzimidazole-5-carboxylate

Database IDs

• CAS Number: 26663-77-4
• MDL Number: MFCD03407310
• PubChem SID: 162035666
• PubChem CID: 2779733

CALCULATED PROPERTIES

• Acid pKa: 11.4997015
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.2192367
• LogD (pH = 7.4): 1.2623631
• Log P: 1.2629809
• Molar Refractivity: 46.9938 cm^3
• Polarizability: 19.06477 Å^3
• Polar Surface Area: 54.98 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 135 - 137°C
• Hydrophobicity(logP): 1.564

Safety Information

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

Product Information

• Purity: 95%; 95+%; 97%; 98%

DETAILS

Toronto Research Chemicals - B197025

An intermediate used for the synthesis of a number of bioisosteric benzimidazoles as inhibitors of human cytosolic phospholipase A2α.

REFERENCES

• Bovens, S., et al.: Bioorg. Med. Chem. Lett., 19, 2107 (2009)