5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid

• ChemBase ID: 67878
• Molecular Formular: C17H11Cl3N2O2
• Molecular Mass: 381.64044
• Monoisotopic Mass: 379.98861064
• SMILES: n1(nc(c(c1c1ccc(cc1)Cl)C)C(=O)O)c1c(cc(cc1)Cl)Cl
• Canonical SMILES: Clc1ccc(cc1)c1c(C)c(nn1c1ccc(cc1Cl)Cl)C(=O)O
• InChI: InChI=1S/C17H11Cl3N2O2/c1-9-15(17(23)24)21-22(14-7-6-12(19)8-13(14)20)16(9)10-2-4-11(18)5-3-10/h2-8H,1H3,(H,23,24)
• InChIKey: CYAYCOCJAVHQSD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid
• IUPAC Traditional name: 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazole-3-carboxylic acid
• Synonyms: 5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazole-3-carboxylic acid; 1-(2,4-Dichlorophenyl)-5-(4-chlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic Acid; 5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic Acid

Database IDs

• CAS Number: 162758-35-2
• MDL Number: MFCD06411080
• PubChem SID: 162033613
• PubChem CID: 1519421

CALCULATED PROPERTIES

• Acid pKa: 2.9397664
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 3.4775832
• LogD (pH = 7.4): 2.513896
• Log P: 5.9952793
• Molar Refractivity: 95.7732 cm^3
• Polarizability: 38.0688 Å^3
• Polar Surface Area: 55.12 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 214-217°C

Safety Information

• Storage Condition: Refrigerator
• Storage Warning: IRRITANT
• TSCA Listed: false

Product Information

• Purity: 95+%

DETAILS

Toronto Research Chemicals - C377830

5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazole-3-carboxylic Acid is used in the preparation of biarylpyrazole based derivatives as cannabinoid CB1 receptor antagonists. It is metabolite M9 of Rimonabant (R517800), an antiobesity agent.

REFERENCES

• Kang, S.Y. et al.: Bioorg. Med. Chem. Lett., 18, 2385 (2008)
• Fulp, A. et al.: Bioorg. Med. Chem. Lett., 21, 5711 (2008)
• Bergstrom, M.A. et al.: Drug Metab. and Dispos., 39, 1823 (2008)