Skip to Content
Merck
CN
All Photos(1)

Key Documents

View All Documentation

Safety Information

V001581

Sigma-Aldrich

p-Toluenesulfonyl chloride

99%

Synonym(s):

Tosyl chloride

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Linear Formula:
CH3C6H4SO2Cl
CAS Number:
98-59-9
Molecular Weight:
190.65
Beilstein:
607898
EC Number:
202-684-8
MDL number:
MFCD00007450

vapor pressure

1 mmHg ( 88 °C)

Quality Level

100

Assay

99%

bp

134 °C/10 mmHg (lit.)

mp

65-69 °C (lit.)

SMILES string

Cc1ccc(cc1)S(Cl)(=O)=O

InChI

1S/C7H7ClO2S/c1-6-2-4-7(5-3-6)11(8,9)10/h2-5H,1H3

InChI key

YYROPELSRYBVMQ-UHFFFAOYSA-N

Looking for similar products? Visit Product Comparison Guide

General description

p-Toluenesulfonyl chloride (tosyl chloride or p-TsCl) is an organic sulfonyl chloride mainly used to convert hydroxyl and amine groups into good leaving groups by forming sulfonates.

Application

p-Toluenesulfonyl chloride can be used as:
  • An additive to enhance the yield of symmetrical biaryls via palladium chloride catalyzed homo-coupling of aryl boronic acids in the absence of ligands.
  • A chlorine source for the α-chlorination of ketones in the presence of LDA.
  • A reactant in the tosylation of alcohols and phenols in the presence of heteropoly acids.
  • An activator for the reaction between 2-alkynylbenzaldoxime and phenols to form 1-aroxyisoquinolines in the presence of silver triflate.
  • A catalyst for the solvent-free preparation of symmetrical bis(benzhydryl)ethers from benzhydrols.

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H290,H315,H317,H318

Hazard Classifications

Eye Dam. 1 - Met. Corr. 1 - Skin Irrit. 2 - Skin Sens. 1

Storage Class Code

8B - Non-combustible corrosive hazardous materials

WGK

WGK 1

Flash Point(F)

262.4 °F - closed cup

Flash Point(C)

128 °C - closed cup

Regulatory Information

新产品

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

Sorry, we don't have COAs for this product available online at this time.

If you need assistance, please contact Customer Support.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Solvent-free and selective tosylation of alcohols and phenols with p-toluenesulfonyl chloride by heteropolyacids as highly efficient catalysts
Fazaeli R, et al.
Canadian Journal of Chemistry, 84(5), 812-818 (2006)
Facile synthesis of symmetrical bis (benzhydryl) ethers using p-toluenesulfonyl chloride under solvent-free conditions
Brahmachari G & Banerjee B
Organic and Medicinal Chemistry Letters, 3(1), 1-1 (2013)
Ligandless palladium chloride-catalyzed homo-coupling of arylboronic acids in aqueous media
Kabalka GW & Wang L.
Tetrahedron Letters, 43(16), 3067-3068 (2002)
Generation of 1-aroxyisoquinolines via a silver-catalyzed reaction of 2-alkynylbenzaldoxime with phenol in the presence of p-toluenesulfonyl chloride
Xiao Q, et al.
Tetrahedron, 69(25), 5119-5122 (2013)
α-Chlorination of ketones using p-toluenesulfonyl chloride.
Brummond KM and Gesenberg KD.
Tetrahedron Letters, 40(12), 2231-2234 (1999)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service