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T35955

Sigma-Aldrich

p-Toluenesulfonyl chloride

reagent grade, ≥98%

Synonym(s):

Tosyl chloride

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About This Item

Linear Formula:
CH3C6H4SO2Cl
CAS Number:
Molecular Weight:
190.65
Beilstein/REAXYS Number:
607898
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.21

grade

reagent grade

Quality Level

vapor pressure

1 mmHg ( 88 °C)

assay

≥98%

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

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Application

p-toluenesulfonyl chloride may be used along with N-methylimidazole for the esterification or thioesterification of carboxylic acids and alcohols or thiols. It may also be used as a chlorine source for α-chlorination of ketones in the presence of lithium diisopropylamide.

pictograms

CorrosionExclamation mark

signalword

Danger

Hazard Classifications

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

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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Rince Wong et al.
The Journal of organic chemistry, 72(10), 3969-3971 (2007-04-21)
A facile and general protocol for the preparation of isothiocyanates from alkyl and aryl amines is reported. This method relies on a tosyl chloride mediated decomposition of a dithiocarbamate salt that is generated in situ by treatment of an amine
Y Tabata et al.
Biomaterials, 7(3), 234-238 (1986-05-01)
The cyanogen bromide (CNBr) activation method was adopted to link collagen molecules onto the surface of cellulose and poly(vinyl alcohol) (PVA) films via covalent bonding. The amount of bound protein was determined by the ninhydrin method and found to be
I M Kung et al.
Biomaterials, 16(8), 649-655 (1995-05-01)
Three different surface modifications were conducted on the membranes of double-layer alginate/poly(L-lysine) microcapsules with tosyl chloride-activated poly(ethylene glycol), cyanuric chloride-activated poly(ethylene glycol) and tosyl chloride-activated poly(vinyl alcohol), separately. All these surface modifications strengthen the microcapsular membranes. Of the three surface-modified
Salvatore Lombardo et al.
Langmuir : the ACS journal of surfaces and colloids, 33(22), 5473-5481 (2017-05-13)
The interaction of bovine serum albumin (BSA) with sulfated, carboxylated, and pyridinium-grafted cellulose nanocrystals (CNCs) was studied as a function of the degree of substitution by determining the adsorption isotherm and by directly measuring the thermodynamics of interaction. The adsorption
Simple, Mild, and Practical esterification, Thioesterification, and amide formation utilizing p-toluenesulfonyl chloride and N-Methylimidazole.
Wakasugi K, et al.
Advanced Synthesis & Catalysis, 345(11), 1209-1214 (2003)

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