Triphenylsulfonium chloride

Triphenylsulfonium chloride Basic information
Product Name:Triphenylsulfonium chloride
Synonyms:TPS-Cl Triphenylsulfonium chloride;’triphenylsulfoniumchloride’solution;Sulfonium,triphenyl-,chloride;triphenyl-sulfoniuchloride;triphenylsulfurchloride;TRIPHENYLSULFONIUM CHLORIDE;triphenylsulphonium chloride;triphenylsulfonium ion
CAS:4270-70-6
MF:C18H15ClS
MW:298.83
EINECS:224-259-6
Product Categories:
Mol File:4270-70-6.mol
Triphenylsulfonium chloride Structure
Triphenylsulfonium chloride Chemical Properties
Melting point 277 °C
storage temp. under inert gas (nitrogen or Argon) at 2-8°C
form powder
color Faint yellow
Water Solubility Soluble in water.
InChIInChI=1S/C18H15S.ClH/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18;/h1-15H;1H/q+1;/p-1
InChIKeyZFEAYIKULRXTAR-UHFFFAOYSA-M
SMILES[S+](C1=CC=CC=C1)(C1=CC=CC=C1)C1C=CC=CC=1.[Cl-]
CAS DataBase Reference4270-70-6(CAS DataBase Reference)
EPA Substance Registry SystemTriphenylsulfonium chloride (4270-70-6)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26
WGK Germany 3
HS Code 2930909899
MSDS Information
ProviderLanguage
SigmaAldrich English
Triphenylsulfonium chloride Usage And Synthesis
UsesTriphenylsulfonium chloride is used as a key intermediate that is widely used in the new electronic chemicals such as semiconductor, LCD and TFT. It is also used as a photoacid generator (PAG) in Catalyst activation through in situ photogeneration of ligands.
PreparationTriphenylsulfonium Chloride Synthesis: Diphenyl sulfoxide, 40 g (0.2 mole), was dissolved in 400 g of dichloroethane, which was stirred under ice cooling. At a temperature below 20° C., 65 g (0.6 mole) of trimethylsilyl chloride was added dropwise to the solution, which was aged for 30 minutes at the temperature. Then, a Grignard reagent which had been prepared from 14.6 g (0.6 mole) of metallic magnesium, 67.5 g (0.6 mole) of chlorobenzene and 168 g of tetrahydrofuran (THF) was added dropwise at a temperature below 20° C. The reaction solution was aged for one hour, after which 50 g of water at a temperature below 20° C. was added to quench the reaction. To this solution, 150 g of water, 10 g of 12N hydrochloric acid, and 200 g of diethyl ether were further added.
The water layer was separated and washed with 100 g of diethyl ether, yielding an aqueous solution of triphenylsulfonium chloride. The compound in aqueous solution form was used in the subsequent reaction without further isolation.
Triphenylsulfonium chloride Preparation Products And Raw materials
Raw materialsChlorotrimethylsilane-->Phenyl sulfoxide-->Chlorobenzene-->Tetrahydrofuran
Methylene Chloride Tributyltin chloride Trichlorine nitride Disulfur dichloride Zinc chloride Titanous chloride Phenyl isothiocyanate Choline chloride Chlorodiphenylphosphine Triphenylsulfonium chloride Sulfuryl chloride Ammonium chloride Chromium(III) chloride Sulfur dichloride Oxalyl chloride Triphenylphosphine Boron trichloride Thionyl chloride

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