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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
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.
α-Chlorination of ketones using p-toluenesulfonyl chloride.
Brummond KM and Gesenberg KD.
Tetrahedron Letters, 40(12), 2231-2234 (1999)
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
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

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