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(Chloromethyl)triphenylphosphonium chloride

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(Chloromethyl)triphenylphosphonium chloride Basic information
Product Name:(Chloromethyl)triphenylphosphonium chloride
Synonyms:(chloromethyl)triphenylphosphonium chliride;Chloromethyl triphenylphosphonium chloride, 98+%;(Chloromethyl)triphenylphosphoniumchloridetech;(CHLOROMETHYL)-TRIPHENYLPHOSPHONIUM CHLORIDE TECH 95%;(Chloromethly)triphenylphosphonium chloride;(Chloromethyl)-triphenylphosphonium chloride, 95%, tech;(Chloromethyl)triphenylphosphonium chloride purum;NSC 93980
CAS:5293-84-5
MF:C19H17Cl2P
MW:347.22
EINECS:226-139-9
Product Categories:Phosphonium Compounds;Synthetic Organic Chemistry;Wittig & Horner-Emmons Reaction;Wittig Reaction;C-C Bond Formation;Olefination;Wittig Reagents
Mol File:5293-84-5.mol
(Chloromethyl)triphenylphosphonium chloride Structure
(Chloromethyl)triphenylphosphonium chloride Chemical Properties
Melting point 262-264 °C (lit.)
storage temp. under inert gas (nitrogen or Argon) at 2-8°C
form Fine Crystalline Powder
color White to almost white
Water Solubility almost transparency
BRN 3599784
InChIInChI=1S/C19H17ClP.ClH/c20-16-21(17-10-4-1-5-11-17,18-12-6-2-7-13-18)19-14-8-3-9-15-19;/h1-15H,16H2;1H/q+1;/p-1
InChIKeySXYFAZGVNNYGJQ-UHFFFAOYSA-M
SMILES[P+](CCl)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cl-]
CAS DataBase Reference5293-84-5(CAS DataBase Reference)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-37/39
WGK Germany 3
RTECS TA1882000
HS Code 29310099
Storage Class11 - Combustible Solids
Hazard ClassificationsEye Irrit. 2
Skin Irrit. 2
STOT SE 3
MSDS Information
ProviderLanguage
SigmaAldrich English
ACROS English
(Chloromethyl)triphenylphosphonium chloride Usage And Synthesis
Chemical Propertieswhite to almost white fine crystalline powder
Uses(Chloromethyl)triphenylphosphonium Chloride is a Wittig reagent.
UsesUsed for corrosion inhibition of iron

Reactant involved in:
  • Acting as a potential electrophile
  • Elimination reactions for the synthesis of linear alkynes
  • Intramolecular nucleophilic vinylic substitution
  • Homologation of aldehydes
  • Endo-selective alkynol cycloisomerization
Preparation(Chloromethyl)triphenylphosphonium chliride is available commercially (chloride or iodide salt) or synthetically from Triphenylphosphine and Chloroiodomethane.
Reactivity Profile(Chloromethyl)triphenylphosphonium chliride is a precursor to the chloro-substituted ylide for Wittig reactions with aldehydes and ketones to form 1-chloroalkenes and, after elimination of HCl, terminal alkynes.
reaction suitabilityreaction type: C-C Bond Formation
PrecautionsFor best results the anhydrous salt should be used. The ylide, formed from the salt and strong base, will react with air, water, or other acidic protons
(Chloromethyl)triphenylphosphonium chloride Preparation Products And Raw materials
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