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422150

Sigma-Aldrich

Triphenylsilanethiol

98%

Synonym(s):

Mercaptotriphenylsilane

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About This Item

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

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

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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.

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

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Tetrahedron Letters, 34, 3363-3363 (1993)

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