3-(6-chloro-5-fluoropyrimidin-4-yl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol

• ChemBase ID: 164693
• Molecular Formular: C16H13ClF3N5O
• Molecular Mass: 383.7555296
• Monoisotopic Mass: 383.0760724
• SMILES: C(C(C(c1ncnc(c1F)Cl)C)(c1c(cc(cc1)F)F)O)n1cncn1
• Canonical SMILES: Fc1ccc(c(c1)F)C(C(c1ncnc(c1F)Cl)C)(Cn1cncn1)O
• InChI: InChI=1S/C16H13ClF3N5O/c1-9(14-13(20)15(17)23-7-22-14)16(26,5-25-8-21-6-24-25)11-3-2-10(18)4-12(11)19/h2-4,6-9,26H,5H2,1H3
• InChIKey: BQDLXFABVRRDFU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(6-chloro-5-fluoropyrimidin-4-yl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol
• IUPAC Traditional name: 3-(6-chloro-5-fluoropyrimidin-4-yl)-2-(2,4-difluorophenyl)-1-(1,2,4-triazol-1-yl)butan-2-ol
• Synonyms: 6-Chloro-α-(2,4-difluorophenyl)-5-fluoro-β-methyl-α-(1H-1,2,4-triazol-1-ylmethyl)-4-pyrimidineethanol; rac-6-Chloro Voriconazole

Database IDs

• CAS Number: 188416-35-5
• PubChem SID: 162258828
• PubChem CID: 11036392

CALCULATED PROPERTIES

• Acid pKa: 12.698382
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 2.647021
• LogD (pH = 7.4): 2.6472492
• Log P: 2.6472545
• Molar Refractivity: 101.1441 cm^3
• Polarizability: 32.789257 Å^3
• Polar Surface Area: 76.72 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White Solid
• Melting Point: 183-187°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - C424200

An achiral intermediate of Voriconazole (V760000).

REFERENCES

• Ferretti, R., et al.: Chromatographia, 47, 649 (1998)