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HomeProduct name listAllyltriphenylphosphonium bromide

Allyltriphenylphosphonium bromide

Synonym(s):2-Propenyltriphenylphosphonium bromide;NSC 110609;NSC 59815

  • CAS NO.:1560-54-9
  • Empirical Formula: C21H20BrP
  • Molecular Weight: 383.26
  • MDL number: MFCD00011808
  • EINECS: 216-332-6
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2023-04-23 13:52:06
Allyltriphenylphosphonium bromide Structural

What is Allyltriphenylphosphonium bromide?

Chemical properties

white crystalline powder

The Uses of Allyltriphenylphosphonium bromide

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.

What are the applications of 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

Properties of Allyltriphenylphosphonium bromide

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
CAS DataBase Reference 1560-54-9(CAS DataBase Reference)

Safety information for Allyltriphenylphosphonium bromide

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P304+P340:IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P405:Store locked up.

Computed Descriptors for Allyltriphenylphosphonium bromide

InChIKey FWYKRJUVEOBFGH-UHFFFAOYSA-M
SMILES [P+](CC=C)(C1C=CC=CC=1)(C1=CC=CC=C1)C1C=CC=CC=1.[Br-]

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