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

• ChemBase ID: 161229
• Molecular Formular: C9H10N2O6S
• Molecular Mass: 274.2505
• Monoisotopic Mass: 274.02595705
• SMILES: c1c(cc2c(c1)nc[nH]2)C(=O)OC.S(=O)(=O)(O)O
• Canonical SMILES: OS(=O)(=O)O.COC(=O)c1ccc2c(c1)[nH]cn2
• InChI: InChI=1S/C9H8N2O2.H2O4S/c1-13-9(12)6-2-3-7-8(4-6)11-5-10-7;1-5(2,3)4/h2-5H,1H3,(H,10,11);(H2,1,2,3,4)
• InChIKey: JEUMRLWTRLNTKZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: sulfuric acid methyl 1H-1,3-benzodiazole-6-carboxylate
• IUPAC Traditional name: sulfuric acid methyl 3H-1,3-benzodiazole-5-carboxylate
• Synonyms: 1H-Benzimidazole-6-carboxylic Acid Methyl Ester Sulfate; Methyl 1H-Benzimidazole-5-carboxylate Sulfate; 1H-Benzimidazole-5-carboxylic Acid Methyl Ester Sulfate

Database IDs

• CAS Number: 131020-58-1
• PubChem SID: 162255364
• PubChem CID: 18985209

CALCULATED PROPERTIES

• Acid pKa: 10.395926
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.0743618
• LogD (pH = 7.4): 1.2594069
• Log P: 1.2629809
• Molar Refractivity: 46.9938 cm^3
• Polarizability: 19.066162 Å^3
• Polar Surface Area: 54.98 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - B197030

The sulfuric acid salt of 1H-Benzimidazole-5-carboxylic Acid Methyl Ester (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)