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240877

Sigma-Aldrich

p-Toluenesulfonyl chloride

ReagentPlus®, ≥99%

Synonym(s):

TsCl, Tosyl chloride

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About This Item

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

vapor pressure

1 mmHg ( 88 °C)

Quality Level

200

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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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
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H290,H315,H317,H318

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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Certificates of Analysis (COA)

Lot/Batch Number
BCCM2067
BCCM0124
MKCT4267
BCCK4643
MKCQ9876

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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)
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)
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)
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