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240877 Sigma-Aldrich

p-Toluenesulfonyl chloride

ReagentPlus®, ≥99%

Synonym: Tosyl chloride, TsCl

  • CAS Number 98-59-9

  • Linear Formula CH3C6H4SO2Cl

  • Molecular Weight 190.65

  •  Beilstein Registry Number 607898

  •  EC Number 202-684-8

  •  MDL number MFCD00007450

  •  PubChem Substance ID 57648053

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Properties

Related Categories Analytical Reagents, Analytical/Chromatography, Chemical Synthesis, Derivatization Reagents, Derivatization Reagents HPLC,
grade   ReagentPlus®
vapor pressure   1 mmHg ( 88 °C)
InChI Key   YYROPELSRYBVMQ-UHFFFAOYSA-N
assay   ≥99%
bp   134 °C/10 mmHg(lit.)
mp   65-69 °C (lit.)
solubility   benzene: freely soluble(lit.)
  chloroform: freely soluble(lit.)
  ethanol: freely soluble(lit.)
  water: insoluble(lit.)

Description

Packaging

100, 500 g in poly bottle

5 g in glass bottle

Application

p-Toluenesulfonyl chloride may be used in the following processes:
• In combination with N-methylimidazole for the esterification or thioesterification of carboxylic acids and alcohols or thiols.
• As an additive to enhance the yield of symmetrical biaryls via palladium chloride catalyzed homo-coupling of arylboronic acids in the absence of ligands.
• As a positive chlorine source for the ?-chlorination of ketones.
• Solvent-free tosylation of alcohols and phenols in the presence of heterodoxy acids.
• As an activator for reaction between 2-alkynylbenzaldoxime and phenols to form 1-aroxyisoquinolines in the presence of silver triflate.
• As a catalyst for the solvent-free preparation of symmetrical bis(benzhydryl)ethers from benzhydrols.

General description

p-Toluenesulfonyl chloride is an organic sulfonyl chloride mainly used to convert hydroxyl groups into good leaving group by forming sulfonates.

Legal Information

ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Precautionary statements 
RIDADR 
UN 3261 8 / PGIII
WGK Germany 
1
RTECS 
DB8929000
Flash Point(F) 
262.4 °F
Flash Point(C) 
128 °C

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Protocols & Articles

Articles

Introduction of Terminal Azide and Alkyne Functionalities in Polymers

“Click” chemistry, and the copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) in particular, is a powerful new synthetic tool in polymer chemistry and material science. Success of the CuAAC in th...
Dr. Joost A. Opsteen
Material Matters 2008, 3.3, 66.
Keywords: Building blocks, Catalysis, Cycloadditions, Esterifications, Materials Science, Nucleophilic substitutions, Polymer science, Polymerization reactions, Radical polymerization, Substitutions, transformation

Peer-Reviewed Papers
15

References

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