240877

p-Toluenesulfonyl chloride

ReagentPlus^®, ≥99%

• Synonym(s): TsCl, Tosyl chloride
• 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

Properties

• 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

Description

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

Safety Information

• Pictograms: GHS05,GHS07
• Signal Word: Danger
• Hazard Statements: H290 - H315 - H317 - H318
• Precautionary Statements: P280 - P302 + P352 - P305 + P351 + P338 + P310
• 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
• Flash Point(C): 128 °C
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves