360031
(Triisopropylsilyl)acetylene
97%
Synonym(s):
Ethynyltriisopropylsilane
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About This Item
Linear Formula:
[(CH3)2CH]3SiC≡CH
CAS Number:
Molecular Weight:
182.38
Beilstein:
3536241
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Assay
97%
form
liquid
refractive index
n20/D 1.4527 (lit.)
bp
50-52 °C/0.6 mmHg (lit.)
density
0.813 g/mL at 25 °C (lit.)
SMILES string
CC(C)[Si](C#C)(C(C)C)C(C)C
InChI
1S/C11H22Si/c1-8-12(9(2)3,10(4)5)11(6)7/h1,9-11H,2-7H3
InChI key
KZGWPHUWNWRTEP-UHFFFAOYSA-N
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General description
Asymmetric addition of (triisopropylsilyl)acetylene to α,β,γ,δ-unsaturated carbonyl compounds in the presence of a cobalt/Duphos catalyst is reported. A Sonogashira coupling reaction between 1-bromo-3-iodo-5-tertbutylbenzene and (triisopropylsilyl)acetylene is reported.
Application
(Triisopropylsilyl)acetylene may be used as reagent for the rhodium-catalyzed asymmetric alkynylation of various α,β-unsaturated ketones. It may be used as reagent in the enantioselective synthesis of β-alkynylated nitroalkanes.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
Storage Class Code
3 - Flammable liquids
WGK
WGK 3
Flash Point(F)
132.8 °F - closed cup
Flash Point(C)
56 °C - closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Takahiro Nishimura et al.
Chemical communications (Cambridge, England), 46(36), 6837-6839 (2010-08-19)
Asymmetric addition of (triisopropylsilyl)acetylene to nitroalkenes took place in the presence of a rhodium/chiral bisphosphine catalyst to give beta-alkynylated nitroalkanes in high yields with high enantioselectivity.
Acetylenic allenophanes: an asymmetric synthesis of a Bis(alleno)-bis(butadiynyl)-meta-cyclophane.
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Angewandte Chemie (International ed. in English), 44(26), 4039-4042 (2005-05-21)
Takahiro Sawano et al.
Journal of the American Chemical Society, 134(46), 18936-18939 (2012-11-08)
Asymmetric addition of (triisopropylsilyl)acetylene to α,β,γ,δ-unsaturated carbonyl compounds took place in the presence of a cobalt/Duphos catalyst to give the 1,6-addition products in high yields with high regio- and enantioselectivity.
Yameng Ren et al.
Advanced science (Weinheim, Baden-Wurttemberg, Germany), 4(9), 1700099-1700099 (2017-09-22)
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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)
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