346977
(Triethylsilyl)acetylene
97%
Synonym(s):
Ethynyltriethylsilane
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About This Item
Linear Formula:
(C2H5)3SiC≡CH
CAS Number:
Molecular Weight:
140.30
Beilstein/REAXYS Number:
1743814
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
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
signalword
Danger
hcodes
Hazard Classifications
Flam. Liq. 2
Storage Class
3 - Flammable liquids
wgk_germany
WGK 3
flash_point_f
62.6 °F - closed cup
flash_point_c
17 °C - closed cup
ppe
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
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Customers Also Viewed
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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