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

• ChemBase ID: 162041
• Molecular Formular: C18H14F4N2O2S
• Molecular Mass: 398.3745728
• Monoisotopic Mass: 398.07121158
• SMILES: c1c(ccc(c1)SCC(O)(C(=O)Nc1ccc(c(c1)C(F)(F)F)C#N)C)F
• Canonical SMILES: N#Cc1ccc(cc1C(F)(F)F)NC(=O)C(CSc1ccc(cc1)F)(O)C
• InChI: InChI=1S/C18H14F4N2O2S/c1-17(26,10-27-14-6-3-12(19)4-7-14)16(25)24-13-5-2-11(9-23)15(8-13)18(20,21)22/h2-8,26H,10H2,1H3,(H,24,25)
• InChIKey: GCGWWKKSGPETMI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfanyl]-2-hydroxy-2-methylpropanamide
• IUPAC Traditional name: N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfanyl]-2-hydroxy-2-methylpropanamide
• Synonyms: (+/-)-N-[4-Cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)thio]-2-hydroxy-2-methyl-propanamide; (R,S)-N-[4-Cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)thio]-2-hydroxy-2-methylpropionamide; Bicalutamide Sulfide; N-(4-Cyano-3-(trifluoromethyl)phenyl)-3-((4-fluorophenyl)thio)-2-hydroxy-2-methylpropanamide

Database IDs

• CAS Number: 90356-78-8
• PubChem SID: 162256176
• PubChem CID: 9800987

CALCULATED PROPERTIES

• Acid pKa: 12.1764765
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 4.0853295
• LogD (pH = 7.4): 4.0853224
• Log P: 4.0853295
• Molar Refractivity: 96.0446 cm^3
• Polarizability: 34.855762 Å^3
• Polar Surface Area: 73.12 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid
• Melting Point: 109-111°C

Safety Information

• Storage Condition: Refrigerator

Product Information

• Purity: 95+%

DETAILS

Toronto Research Chemicals - B382040

Bicalutamide intermediate.

REFERENCES

• Tucker, H., et al.: J. Med. Chem., 31, 954 (1988)
• Rao, R., et al.: J. Pharm. Biomed. Anal., 46, 505 (1988)