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Merck

240877

p-Toluenesulfonyl chloride

≥99%, solid, ReagentPlus®

Synonym(s):

TsCl, Tosyl chloride

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About This Item

Linear Formula:
CH3C6H4SO2Cl
CAS Number:
98-59-9
Molecular Weight:
190.65
NACRES:
NA.21
PubChem Substance ID:
57648053
UNSPSC Code:
12352100
EC Number:
202-684-8
MDL number:
MFCD00007450
Beilstein/REAXYS Number:
607898

Product Name

p-Toluenesulfonyl chloride, ReagentPlus®, ≥99%

InChI key

YYROPELSRYBVMQ-UHFFFAOYSA-N

InChI

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

SMILES string

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

vapor pressure

1 mmHg ( 88 °C)

product line

ReagentPlus®

assay

≥99%

form

solid

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.)

Quality Level

200

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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 Merck KGaA, Darmstadt, Germany

pictograms

CorrosionExclamation mark
GHS05,GHS07

signalword

Danger

Hazard Classifications

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

Storage Class

8B - Non-combustible corrosive hazardous materials

wgk

WGK 1

flash_point_f

262.4 °F - closed cup

flash_point_c

128 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN5305
BCCM2067
BCCM0124
MKCT4267
BCCK4643

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Immobilization of ligands with organic sulfonyl chlorides
Nilsson K & Mosbach K
Methods in Enzymology, 104, 56-69 (1984)
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)
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)
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)
Ligandless palladium chloride-catalyzed homo-coupling of arylboronic acids in aqueous media
Kabalka GW & Wang L.
Tetrahedron Letters, 43(16), 3067-3068 (2002)
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