3-(benzenesulfonyl)-N-[4-cyano-3-(trifluoromethyl)phenyl]-2-hydroxy-2-methylpropanamide

• ChemBase ID: 166275
• Molecular Formular: C18H15F3N2O4S
• Molecular Mass: 412.3829096
• Monoisotopic Mass: 412.07046263
• SMILES: c1c(c(ccc1NC(=O)C(CS(=O)(=O)c1ccccc1)(O)C)C#N)C(F)(F)F
• Canonical SMILES: N#Cc1ccc(cc1C(F)(F)F)NC(=O)C(CS(=O)(=O)c1ccccc1)(O)C
• InChI: InChI=1S/C18H15F3N2O4S/c1-17(25,11-28(26,27)14-5-3-2-4-6-14)16(24)23-13-8-7-12(10-22)15(9-13)18(19,20)21/h2-9,25H,11H2,1H3,(H,23,24)
• InChIKey: GDXNOJUTJPBYEC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(benzenesulfonyl)-N-[4-cyano-3-(trifluoromethyl)phenyl]-2-hydroxy-2-methylpropanamide
• IUPAC Traditional name: 3-(benzenesulfonyl)-N-[4-cyano-3-(trifluoromethyl)phenyl]-2-hydroxy-2-methylpropanamide
• Synonyms: (+/-)-N-[4-Cyano-3-(trifluoromethyl)phenyl]-2-hydroxy-2-methyl-3-(phenylsulfonyl)propanamide; Desfluoro Bicalutamide

Database IDs

• CAS Number: 90357-05-4
• PubChem SID: 162260408
• PubChem CID: 10112342

CALCULATED PROPERTIES

• Acid pKa: 11.947142
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 2.5665934
• LogD (pH = 7.4): 2.5665815
• Log P: 2.5665936
• Molar Refractivity: 96.3731 cm^3
• Polarizability: 36.304005 Å^3
• Polar Surface Area: 107.26 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Methanol
• Apperance: Off-White Solid
• Melting Point: 171-174°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - D289955

Bicalutamide impurity. A nonsteroidal antiandrogen.

REFERENCES

• Tucker, H., et al.: J. Med. Chem., 31, 954 (1988)