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Sigma-Aldrich

(Triphenylsilyl)acetylene

98%

Synonym(s):

1,1′,1′′-(Ethynylsilylidyne)tris[benzene], Ethynyltriphenylsilane, Triphenylsilylacetylene, Triphenylsilylethyne

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About This Item

Linear Formula:
(C6H5)3SiC≡CH
CAS Number:
6229-00-1
Molecular Weight:
284.43
MDL number:
MFCD00075453
UNSPSC Code:
12352100
PubChem Substance ID:
24862140
NACRES:
NA.22

Quality Level

100

Assay

98%

mp

48-50 °C (lit.)

SMILES string

C#C[Si](c1ccccc1)(c2ccccc2)c3ccccc3

InChI

1S/C20H16Si/c1-2-21(18-12-6-3-7-13-18,19-14-8-4-9-15-19)20-16-10-5-11-17-20/h1,3-17H

InChI key

WADKYPSVXRWORK-UHFFFAOYSA-N

General description

(Triphenylsilyl)acetylene is a terminal alkyne. Rhodium-catalyzed asymmetric addition of (triphenylsilyl)acetylene to diphenylphosphinylallene is reported.

Application

(Triphenylsilyl)acetylene may be used in the synthesis of:
  • selenothioic acid S-alkyl esters
  • methyl 2-(di{ 3, 5-bis[(triphenylsilyl)ethynyl]phenyl}-phosphino)benzoate
  • 2-(di{3,5-bis[(triphenylsilyl)ethynyl]phenyl}-phosphino)benzoic acid

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Takahiro Nishimura et al.
Chemistry, an Asian journal, 3(8-9), 1505-1510 (2008-05-09)
The presence of an acid was found to be essential in the rhodium-catalyzed asymmetric addition of terminal alkynes to diarylphosphinylallenes giving exo-enynes in high yields with high regio- and enantioselectivity. The stereochemical outcome is determined at the protonolysis of the
Selenothioic acid S-esters: Synthesis, characterization, and trend for stability.
Murai T, et al.
Journal of the American Chemical Society, 119(37), 8592-8597 (1997)
Crafting chiral space. The synthesis of C~ 2-symmetric diphosphine ligands for an outer-sphere catalytic reaction.
Trost BM and Marschner C.
Bulletin de la Societe Chimique De France, 134, 263-274 (1997)

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