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346977

Sigma-Aldrich

(Triethylsilyl)acetylene

97%

Synonym(s):

Ethynyltriethylsilane

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About This Item

Linear Formula:
(C2H5)3SiC≡CH
CAS Number:
1777-03-3
Molecular Weight:
140.30
Beilstein:
1743814
MDL number:
MFCD00075373
UNSPSC Code:
12352100
PubChem Substance ID:
24861453
NACRES:
NA.22

Assay

97%

form

liquid

refractive index

n20/D 1.433 (lit.)

density

0.783 g/mL at 25 °C (lit.)

SMILES string

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

InChI

1S/C8H16Si/c1-5-9(6-2,7-3)8-4/h1H,6-8H2,2-4H3

InChI key

FWSPXZXVNVQHIF-UHFFFAOYSA-N

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General description

(Triethylsilyl)acetylene, a bulky trialkylsilyl-protected alkyne, undergoes Cadiot-Chodkiewicz cross-coupling reaction with various bromoalkynes to yield synthetically useful unsymmetrical diynes. Rhodium-catalyzed dimerization of (triethylsilyl)acetylene has been reported.

Application

(Triethylsilyl)acetylene may be used in the synthesis of triethylsilylethynyl anthradithiophenes, such as :
  • 2,8-dimethyl-5,11-bis(triethylsilylethynyl)ADT (ADT= anthradithiophene)
  • 2,8-diethyl-5,11-bis(triethylsilylethynyl)ADT
  • 2,8-dipropyl-5,11-bis(triethylsilylethynyl)ADT

Pictograms

Flame
GHS02

Signal Word

Danger

Hazard Statements

H225

Precautionary Statements

P210 - P370 + P378 - P403 + P235

Hazard Classifications

Flam. Liq. 2

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

62.6 °F - closed cup

Flash Point(C)

17 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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hin-film morphology and transistor performance of alkyl-substituted triethylsilylethynyl anthradithiophenes.
Anthony JE, et al.
Journal of Materials Chemistry, 19(42), 7984-7989 (2009)
Steric tuning of silylacetylenes and chiral phosphine ligands for rhodium-catalyzed asymmetric conjugate alkynylation of enones.
Takahiro Nishimura et al.
Journal of the American Chemical Society, 130(5), 1576-1577 (2008-01-17)
Joseph P Marino et al.
The Journal of organic chemistry, 67(19), 6841-6844 (2002-09-14)
Bulky trialkylsilyl-protected alkynes such as triethylsilyl (TES), tert-butyldimethylsilyl (TBS), and triisopropylsilyl (TIPS) acetylenes underwent the Cadiot-Chodkiewicz cross-coupling reaction with different bromoalkynes to form a variety of synthetically useful unsymmetrical diynes in good yields. The diyne alcohol 10 was transformed regio-

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