triphenyl[(E)-2-(triphenylphosphaniumyl)ethenyl]phosphanium dibromide

• ChemBase ID: 301876
• Molecular Formular: C38H32Br2P2
• Molecular Mass: 710.416202
• Monoisotopic Mass: 708.03459828
• SMILES: c1ccc(cc1)[P+](/C=C/[P+](c1ccccc1)(c1ccccc1)c1ccccc1)(c1ccccc1)c1ccccc1.[Br-].[Br-]
• Canonical SMILES: c1ccc(cc1)[P+](c1ccccc1)(c1ccccc1)/C=C/[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Br-].[Br-]
• InChI: InChI=1S/C38H32P2.2BrH/c1-7-19-33(20-8-1)39(34-21-9-2-10-22-34,35-23-11-3-12-24-35)31-32-40(36-25-13-4-14-26-36,37-27-15-5-16-28-37)38-29-17-6-18-30-38;;/h1-32H;2*1H/q+2;;/p-2/b32-31+
• InChIKey: TVFYBHGFLHYJNV-GLDAUVFXSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: triphenyl[(E)-2-(triphenylphosphaniumyl)ethenyl]phosphanium dibromide
• IUPAC Traditional name: triphenyl[(E)-2-(triphenylphosphaniumyl)ethenyl]phosphanium dibromide
• Synonyms: 1,2-Vinylenebis(triphenylphosphonium bromide) monohydrate; 1,2-亚乙烯基双(三苯基溴化膦)单水合物

Database IDs

• CAS Number: 54770-27-3
• EC Number: 259-334-2
• MDL Number: MFCD00040548
• Beilstein Number: 3583793

CALCULATED PROPERTIES

• Acid pKa: 17.832264
• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 8.5896
• LogD (pH = 7.4): 8.5896
• Log P: 8.5896
• Molar Refractivity: 172.2346 cm^3
• Polarizability: 67.90609 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: ca 236-250°C

Safety Information

• Storage Warning: Hygroscopic
• European Hazard Symbols: Irritant (Xi)
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A

Product Information

• Purity: 98%

REFERENCES

• Conjugate addition of alcohols in the presence of triethylamine, followed by elimination and removal of the second phosphonium salt by base-induced cleavage, leads to vinyl ethers: Synthesis, 736 (1975). Similarly, other nucleophiles (e.g. phenols or thiols) can be used to replace one of the phosphonium groups by addition-elimination: Bull. Soc. Chim. Fr., 1421 (1974). With bifunctional nucleophiles, cyclization can occur to give an intermediate for the formylolefination of aldehydes by the Wittig reaction: Synthesis, 826 (1978):