422150

Triphenylsilanethiol

98%

• Synonym(s): Mercaptotriphenylsilane
• Linear Formula: (C₆H₅)₃SiSH
• CAS Number: 14606-42-9
• Molecular Weight: 292.47
• Beilstein/REAXYS Number: 2941369
• MDL number: MFCD00192551
• UNSPSC Code: 12352103
• PubChem Substance ID: 24866296
• NACRES: NA.22

Properties

• assay: 98%
• mp: 101-104 °C (lit.)
• SMILES string: S[Si](c1ccccc1)(c2ccccc2)c3ccccc3
• InChI: 1S/C18H16SSi/c19-20(16-10-4-1-5-11-16,17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15,19H
• InChI key: MQDRKELSDPESDZ-UHFFFAOYSA-N

Description

General description

Triphenylsilanethiol, also known as triphenylsilyl mercaptan, is an organosilicon compound that is commonly used as a reagent in organic synthesis. It can be used as a reagent for palladium-catalyzed cross-coupling reactions, such as the Stille coupling and the Sonogashira coupling reactions.

Application

Triphenylsilanethiol can be used as:      

• A reactant to synthesis β-hydroxymercaptans or β-dihydroxysulfides by ring opening of epoxides.      
• An additive in the selective C–H bond functionalization of widely available trialkylamine scaffolds.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)