399264
(tert-Butyldimethylsilyl)acetylene
99%
Synonym(s):
Ethynyl-tert-butyldimethylsilane
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About This Item
Linear Formula:
(CH3)3CSi(CH3)2C≡CH
CAS Number:
Molecular Weight:
140.30
Beilstein/REAXYS Number:
1921466
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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assay
99%
refractive index
n20/D 1.451 (lit.)
bp
116-117 °C (lit.)
density
0.751 g/mL at 25 °C (lit.)
SMILES string
CC(C)(C)[Si](C)(C)C#C
InChI
1S/C8H16Si/c1-7-9(5,6)8(2,3)4/h1H,2-6H3
InChI key
RTYNRTUKJVYEIE-UHFFFAOYSA-N
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General description
(tert-Butyldimethylsilyl)acetylene is a bulky trialkylsilyl-protected alkyne. It participates in Cadiot-Chodkiewicz cross-coupling reaction with various bromoalkynes to afford synthetically useful unsymmetrical diynes.
(tert-Butyldimethylsilyl)acetylene readily undergoes cross-dimerization reaction with various internal phenyl acetylenes in the presence of rhodium dimers and bidentate phosphine ligands to afford enynes.
application
(tert-Butyldimethylsilyl)acetylene may be used in the synthesis of β-alkynylketone and β-alkynyl aldehydes.
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Trost BM and Li CJ.
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Asymmetric synthesis of beta-alkynyl aldehydes by rhodium-catalyzed conjugate alkynylation.
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Angewandte Chemie (International ed. in English), 48(43), 8057-8059 (2009-09-22)
Steric tuning of silylacetylenes and chiral phosphine ligands for rhodium-catalyzed asymmetric conjugate alkynylation of enones.
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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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