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240877

Sigma-Aldrich

p-Toluenesulfonyl chloride

ReagentPlus®, ≥99%

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Synonym(s):
TsCl, Tosyl chloride
Linear Formula:
CH3C6H4SO2Cl
CAS Number:
Molecular Weight:
190.65
Beilstein/REAXYS Number:
607898
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.21

vapor pressure

1 mmHg ( 88 °C)

Quality Level

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.)

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

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1 of 4

This Item
T359555663578.08326
vibrant-m

240877

p-Toluenesulfonyl chloride

vibrant-m

T35955

p-Toluenesulfonyl chloride

vibrant-m

566357

m-Toluenesulfonyl chloride

vibrant-m

8.08326

4-Toluenesulfonyl chloride

assay

≥99%

assay

≥98%

assay

97%

assay

≥98.0% (GC)

solubility

benzene: freely soluble(lit.), ethanol: freely soluble(lit.), chloroform: freely soluble(lit.), water: insoluble(lit.)

solubility

-

solubility

-

solubility

-

bp

134 °C/10 mmHg (lit.)

bp

134 °C/10 mmHg (lit.)

bp

252-253 °C (lit.)

bp

-

form

solid

form

-

form

-

form

solid

mp

65-69 °C (lit.)

mp

65-69 °C (lit.)

mp

-

mp

67 °C

General description

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

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.

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

pictograms

CorrosionExclamation mark

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_germany

WGK 1

flash_point_f

262.4 °F

flash_point_c

128 °C

ppe

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


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Customers Also Viewed

Slide 1 of 4

1 of 4

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)
Immobilization of ligands with organic sulfonyl chlorides
Nilsson K & Mosbach K
Methods in Enzymology, 104, 56-69 (1984)
Haibo Mu et al.
Nature communications, 10(1), 4039-4039 (2019-09-08)
Antibiotic therapy is usually not recommended for salmonellosis, as it is associated with prolonged fecal carriage without reducing symptom duration or severity. Here we show that antibiotics encapsulated in hydrogen sulfide (H2S)-responsive glycovesicles may be potentially useful for the treatment
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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