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Vinyltriphenylphosphonium bromide

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Vinyltriphenylphosphonium bromide Basic information
Uses
Product Name:Vinyltriphenylphosphonium bromide
Synonyms:TRIPHENYLVINYLPHOSPHONIUM BROMIDE;Schweizers;Schweizer'sReagent~Triphenylvinylphosphoniumbromide;Vinyltriphenylphosphoniumbromide,97%;Vinylteriphenylphosphonium bromide;Phosphonium, ethenyltriphenyl-, bromide;VINYL TRIPHENYLPHOSPHONIUM BROMIDE (TRIPHENYL VINYLPHOSPHONIUM BROMIDE);Schweizers Reagent, Vinyltriphenylphosphonium bromide
CAS:5044-52-0
MF:C20H18BrP
MW:369.24
EINECS:225-740-3
Product Categories:Phosphonium Compounds;Synthetic Organic Chemistry;Wittig & Horner-Emmons Reaction;Wittig Reaction
Mol File:5044-52-0.mol
Vinyltriphenylphosphonium bromide Structure
Vinyltriphenylphosphonium bromide Chemical Properties
Melting point 176-178 °C (lit.)
storage temp. 2-8°C
form solid
AppearanceWhite to off-white Solid
Sensitive Light Sensitive & Hygroscopic
BRN 4168860
InChIInChI=1S/C20H18P.BrH/c1-2-21(18-12-6-3-7-13-18,19-14-8-4-9-15-19)20-16-10-5-11-17-20;/h2-17H,1H2;1H/q+1;/p-1
InChIKeyVRAYVWUMBAJVGH-UHFFFAOYSA-M
SMILES[P+](C1C=CC=CC=1)(C1C=CC=CC=1)(C1C=CC=CC=1)C=C.[Br-]
CAS DataBase Reference5044-52-0(CAS DataBase Reference)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 22-24/25
WGK Germany 3
Storage Class11 - Combustible Solids
MSDS Information
ProviderLanguage
SigmaAldrich English
ACROS English
ALFA English
Vinyltriphenylphosphonium bromide Usage And Synthesis
UsesTriphenylvinylphosphonium Bromide has been used to enhance the thermal stability of epoxy resin. It is commonly used as a Wittig reagent.
Chemical PropertiesWHITE TO BEIGE FINE CRYSTALLINE POWDER
UsesReactant involved in:
  • Asymmetric conjugate addition and intramolecular cyclization
  • Condensation with benzoxazinediones
  • Intramolecular dehydrobromination
  • Schweizer reaction
  • Cycloaddition with nitro ketone Baylis-Hillman adducts
', 'Reagent for the synthesis of heterocycles.
PreparationThe preparation of TriphenylvinylphosphoniuM BroMide has been accomplished by treatment of ethylenebis(triphenylphosphonium) dibromide with borate ion (32%), (2-chloroethyl)triphenylphosphonium bromide with Triethylamine (72%), (2-bromoethyl)triphenylphosphonium bromide with Silver(I) Oxide (85%), and (2- phenoxyethyl)triphenylphosphonium bromide with boiling ethyl acetate (92%).
reaction suitabilityreaction type: C-C Bond Formation
storagehygroscopic; irritant; produces sneezing in many individuals. Use in a fume hood.
Vinyltriphenylphosphonium bromide Preparation Products And Raw materials
Tag:Vinyltriphenylphosphonium bromide(5044-52-0) Related Product Information
Triphenylvinylsilane Triphenyltridecylphosphonium Bromide Bromodimethylsulfonium bromide Aniline ((2-(Ethoxycarbonyl)-1-phenyl)ethenyl)triphenylphosphonium bromide Vinyltriphenylphosphonium bromide 1,2-VINYLENEBIS(TRIPHENYLPHOSPHONIUM BROMIDE) (1,3-BUTADIENYL)TRIPHENYLPHOSPHONIUM BROMIDE