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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:
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

Signal Word

Danger

Hazard Statements

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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
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
Katarzyna Dziarkowska et al.
Analytica chimica acta, 606(2), 184-193 (2007-12-18)
Determination of polyamines in biological fluids possesses medical diagnostic relevance. Despite the vast panel of analytical methods developed for polyamines they are not applied in routine clinical usage, mainly due to the time and labor consuming sample preparation step and
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)
Maxim V Khrolenko et al.
Journal of chromatography. A, 1093(1-2), 111-117 (2005-10-20)
The application of supported-liquid membrane (SLM) technique for effective extraction of N-(phosphonomethyl)glycine (glyphosate) and its primary metabolite aminomethylphosphonic acid (AMPA) from juices (orange, grapefruit, apple and blackcurrant) in combination with HPLC-UV detection after derivatization with p-toluenesulphonyl chloride (TsCl) is presented.

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