Allyltriphenylphosphonium bromide Chemical Properties

Melting point:

222-225 °C (lit.)

storage temp. 

Sealed in dry,Room Temperature

form 

Powder

color 

White

Water Solubility 

decomposes

Sensitive 

Hygroscopic

BRN 

3579053

InChI

InChI=1S/C21H20P.BrH/c1-2-18-22(19-12-6-3-7-13-19,20-14-8-4-9-15-20)21-16-10-5-11-17-21;/h2-17H,1,18H2;1H/q+1;/p-1

InChIKey

FWYKRJUVEOBFGH-UHFFFAOYSA-M

SMILES

[P+](CC=C)(C1C=CC=CC=1)(C1=CC=CC=C1)C1C=CC=CC=1.[Br-]

CAS DataBase Reference

1560-54-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

RTECS 

TA1843000

HS Code 

29310095

Toxicity

mouse,LD50,intravenous,22mg/kg (22mg/kg),U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#01708,

MSDS

• Language:English Provider:Allyltriphenylphosphonium bromide
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
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Allyltriphenylphosphonium bromide Usage And Synthesis

Chemical Properties

white crystalline powder

Uses

Allyltriphenylphosphonium bromide is used for the first time in the preparation of DES. It has been shown to be part of Phosphonium salts, having antiviral activity against influenza virus A. It can be used in witting olefination of aldehydes for preparation of conjugated dienes.

Preparation

Allyltriphenylphosphonium bromide was synthesized from the reaction of triphenylphosphine and allyl bromide in dry toluene.

Application

Reactant for:
Preparation of a diol and carbamate chemistry library for common functional groups
Regioselective synthesis of alkenes via semihydrogenation and semihydrogenation-oxidation of dienes
Alkene addition of frustrated Lewis pairs
Olefination of N-sulfonyl imines for stereoselective synthesis of vinyl arenes
Wittig olefination of aldehydes for preparation of conjugated dienes
Tandem Michael addition / ylide olefination reactions for the synthesis of highly functionalized cyclohexadienes
Reaction of allyltriphenylphosphonium bromide and Garner's aldehyde in basic media provided β- hydroxy-1,3-dienes.
Methyl 3-(buta-1,3-dienyl)benzoate
1-(Buta-1,3-dienyl)-4-(trifluoromethyl)benzene
1-(Buta-1,3-dienyl)-2-chlorobenzene
1-Bromo-4-(buta-1,3-dienyl)benzene
Buta-1,3-dienylbenzene

Allyltriphenylphosphonium bromide(1560-54-9)Related Product Information

• Triphenylphosphine hydrobromide
• Dimidium bromide
• TETRAPHENYLPHOSPHINE IMIDE
• Triphenylphosphine
• Rocuronium bromide
• Tetraphenylphosphonium bromide
• Triphenylphosphine oxide
• Tris(triphenylphosphine)rhodiu
• Tetrakis(triphenylphosphine)palladium
• Sodium bromate
• Vecuronium bromide
• Tetrapropylammonium bromide
• Allyl bromide
• Methyltriphenylphosphonium bromide
• Ethidium bromide
• Allyl triphenylphosphonium chloride
• ALLYLTRIPHENYLTIN
• Allyltrimethylsilane