V001581

p-Toluenesulfonyl chloride

99%

• Synonym(s): Tosyl chloride
• Linear Formula: CH₃C₆H₄SO₂Cl
• CAS Number: 98-59-9
• Molecular Weight: 190.65
• Beilstein/REAXYS Number: 607898
• EC Number: 202-684-8
• MDL number: MFCD00007450

Properties

• vapor pressure: 1 mmHg ( 88 °C)
• Quality Level: 100
• assay: 99%
• 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

Description

General description

p-Toluenesulfonyl chloride (tosyl chloride or p-TsCl) is an organic sulfonyl chloride mainly used to convert hydroxyl and amine groups into good leaving groups by forming sulfonates.[1]

Application

p-Toluenesulfonyl chloride can be used as:

• An additive to enhance the yield of symmetrical biaryls via palladium chloride catalyzed homo-coupling of aryl boronic acids in the absence of ligands.[2]
• A chlorine source for the α-chlorination of ketones in the presence of LDA.[3]
• A reactant in the tosylation of alcohols and phenols in the presence of heteropoly acids.[1]
• An activator for the reaction between 2-alkynylbenzaldoxime and phenols to form 1-aroxyisoquinolines in the presence of silver triflate.[4]
• A catalyst for the solvent-free preparation of symmetrical bis(benzhydryl)ethers from benzhydrols.[5]

Safety Information

• pictograms: GHS05,GHS07
• signalword: Danger
• hcodes: H290,H315,H317,H318
• pcodes: P280 - P302 + P352 - P305 + P351 + P338 + P310
• Hazard Classifications: Eye Dam. 1 - Met. Corr. 1 - Skin Irrit. 2 - Skin Sens. 1
• Storage Class: 8B - Non-combustible corrosive hazardous materials
• wgk_germany: WGK 1
• flash_point_f: 262.4 °F - closed cup
• flash_point_c: 128 °C - closed cup