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218170

Sigma-Aldrich

Ethynyltrimethylsilane

98%

Synonym(s):

Trimethylsilylacetylene

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About This Item

Linear Formula:
(CH3)3SiC≡CH
CAS Number:
1066-54-2
Molecular Weight:
98.22
Beilstein:
906752
MDL number:
MFCD00008569
UNSPSC Code:
12352100
PubChem Substance ID:
24853048
NACRES:
NA.22

vapor pressure

4.18 psi ( 20 °C)

Assay

98%

form

liquid

refractive index

n20/D 1.388 (lit.)

bp

53 °C (lit.)

density

0.709 g/cm3 (lit.)

storage temp.

2-8°C

SMILES string

C[Si](C)(C)C#C

InChI

1S/C5H10Si/c1-5-6(2,3)4/h1H,2-4H3

InChI key

CWMFRHBXRUITQE-UHFFFAOYSA-N

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General description

Laser-induced polymerization of gaseous ethynyltrimethylsilane was used for efficient chemical vapour deposition of polycarbosilane films. Ethynyltrimethylsilane acts as substrate for nickel-catalyzed cross-coupling with benzonitriles.

Application

Ethynyltrimethylsilane was used in:
  • microwave-assisted, one-pot, three-step Sonogashira cross-coupling-desilylation-cycloaddition reaction for the preparation of 1,4-disubstituted 1,2,3-triazoles
  • synthesis of poly(ethynyltrimethylsilane) containing Pd (II) coordination sites
  • pyrazole synthesis via 1,3-dipolar cycloaddition of diazo compounds to acetylenes

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Danger

Hazard Statements

H225,H315,H319

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 2 - Skin Irrit. 2

Storage Class Code

3 - Flammable liquids

WGK

WGK 1

Flash Point(F)

-29.2 °F

Flash Point(C)

-34 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Frédéric Friscourt et al.
Organic letters, 12(21), 4936-4939 (2010-10-15)
A microwave-assisted, one-pot, three-step Sonogashira cross-coupling-desilylation-cycloaddition sequence was developed for the convenient preparation of 1,4-disubstituted 1,2,3-triazoles starting from a range of halides, acyl chlorides, ethynyltrimethylsilane, and azides.
Francisco J Caparrós et al.
Molecules (Basel, Switzerland), 25(4) (2020-02-26)
A new 2,7,10,15-tetraethynyldibenzo[g,p]chrysene ligand (1) and two tetranuclear gold(I) derivatives containing PPh3 (3) and PMe3 (4) phosphines were synthesized and characterized by 1H and 31P NMR, IR spectroscopy, and high-resolution mass spectrometry. The compounds were studied in order to analyze
Tetrahedron Letters, 45, 4989-4992 (2004)
Atmospheric pressure chemical vapour deposition of polycarbosilane films via UV laser-induced polymerization of ethynyltrimethylsilane.
Pola J, et al.
Surface and Coating Tech., 149(2), 129-134 (2002)
Fabian Reiß et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 24(21), 5667-5674 (2018-02-02)
The reaction of the allene precursor Li2 (Me3 SiC3 SiMe3 ) with [Cp2 ZrCl2 ] (Cp=cyclopentadienyl) was examined. The selective formation of hitherto unknown linear, allene-bridged dizirconocene complexes [(Cp2 ZrCl)2 {-μ-(Me3 Si)C3 (SiMe3 )-}] and [(Cp2 Zr)2 {-μ-(Me3 Si)C3 (SiMe3
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