Vinyltriphenylphosphonium bromide

• Catalog No.: L00708
• CAS Number: 5044-52-0
• M. F.: C20H18BrP
• M. W.: 369.234681
• Purity: 97%

SYNONYMS

• Title: 溴化乙烯基三苯基膦
• IUPAC name: ethenyltriphenylphosphanium bromide
• IUPAC Traditional name: ethenyltriphenylphosphanium bromide
• Synonyms: Schweizer's Reagent; Triphenylvinylphosphonium bromide

DATABASE IDS

• Beilstein Number: 4168860
• MDL Number: MFCD00011807
• EC Number: 225-740-3
• CAS Number: 5044-52-0

PROPERTIES

• Purity: 97%
• Melting Point: 182-186°C
• GHS Hazard statements: H315-H319-H335
• European Hazard Symbols: Irritant (Xi)
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• Storage Warning: Light Sensitive & Hygroscopic
• TSCA Listed: 否

REFERENCES

• Conjugate additions of nucleophiles to the double bond give ?-substituted ethyl triphenylphosphonium salts which can be further reacted by Wittig olefination. Sequential reaction with phthalimide and an aldehyde leads, after hydrazinolysis of the resulting N-allylphthalimide, to 3-substituted allylamines: J. Org. Chem., 46, 3119 (1981). N-Alkyl allylamines can also be prepared from alkylamines: Tetrahedron Lett., 24, 3043 (1983):
  
• A variety of heterocyclic systems can be synthesized by conjugate addition and subsequent Wittig condensation: J. Am. Chem. Soc., 86, 2744, 2963 (1964); J. Org. Chem., 33, 2416 (1968). Use of carbon nucleophiles permits synthesis of carbocyclic systems: J. Org. Chem., 30, 2082 (1965).
• Conjugate addition of organocuprates leads to a new phosphonium salt which can be used in the Wittig olefination. With alkenyl cuprates this provides a stereoselective route to (Z,Z)-1,4-pentadienes: Tetrahedron Lett., 26, 1799 (1985). Sequential reactions, catalyzed by CuBr - Ag₂CO₃ or CuBr - H₂O, with Grignard reagents and Wittig olefination with an aldehyde, have also been reported: J. Org. Chem., 61,9659 (1996):