[(4-methoxy-2-nitrophenyl)methyl]triphenylphosphanium bromide

• ChemBase ID: 173071
• Molecular Formular: C26H23BrNO3P
• Molecular Mass: 508.343481
• Monoisotopic Mass: 507.05989223
• SMILES: c1c(ccc(c1[N+](=O)[O-])C[P+](c1ccccc1)(c1ccccc1)c1ccccc1)OC.[Br-]
• Canonical SMILES: COc1ccc(c(c1)[N+](=O)[O-])C[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Br-]
• InChI: InChI=1S/C26H23NO3P.BrH/c1-30-22-18-17-21(26(19-22)27(28)29)20-31(23-11-5-2-6-12-23,24-13-7-3-8-14-24)25-15-9-4-10-16-25;/h2-19H,20H2,1H3;1H/q+1;/p-1
• InChIKey: UOGAUEAECQVDOW-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: [(4-methoxy-2-nitrophenyl)methyl]triphenylphosphanium bromide
• IUPAC Traditional name: [(4-methoxy-2-nitrophenyl)methyl]triphenylphosphanium bromide
• Synonyms: [(4-Methoxy-2-nitrophenyl)methyl]triphenylphosphonium Bromide

Database IDs

• CAS Number: 886442-56-4
• PubChem SID: 164228981
• PubChem CID: 71623641

CALCULATED PROPERTIES

• Acid pKa: 15.325776
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 6.134577
• LogD (pH = 7.4): 6.134577
• Log P: 6.134577
• Molar Refractivity: 125.6217 cm^3
• Polarizability: 48.286068 Å^3
• Polar Surface Area: 55.05 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol

DETAILS

Toronto Research Chemicals - M264980

[(4-Methoxy-2-nitrophenyl)methyl]triphenylphosphonium bromide is used in the synthesis of Combretastatin A4 (C643000) substituents (nitro or serinamide substituents) as inhibitors of tubulin assembly and vascular disrupting agents.

REFERENCES

• Monk, K., et al.: Bioorg. Med. Chem., 14, 3231 (2006)
• Hall, J., et al.: Bioorg. Med. Chem. Lett., 18, 5146 (2006)