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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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 1 petroleums
Hazardous rank II
Water insoluble liquid

JAN Code

346977-VAR:
346977-25G:
346977-BULK:
346977-5G:
346977-1G:

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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hin-film morphology and transistor performance of alkyl-substituted triethylsilylethynyl anthradithiophenes.
Anthony JE, et al.
Journal of Materials Chemistry, 19(42), 7984-7989 (2009)
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-
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)

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