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Sigma-Aldrich

(Triisopropylsilyl)acetylene

97%

Synonym(s):

Ethynyltriisopropylsilane

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About This Item

Linear Formula:
[(CH3)2CH]3SiC≡CH
CAS Number:
89343-06-6
Molecular Weight:
182.38
Beilstein/REAXYS Number:
3536241
MDL number:
MFCD00075452
UNSPSC Code:
12352100
PubChem Substance ID:
24862139
NACRES:
NA.22

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.

pictograms

FlameExclamation mark
GHS02,GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

132.8 °F - closed cup

flash_point_c

56 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

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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.
Matthew D Clay et al.
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)
Continuous studies on the use of a polycyclic aromatic hydrocarbon as the central block of an organic photosensitizer have brought forth a new opportunity toward efficiency enhancement of dye-sensitized solar cells (DSCs). In this paper, a nonacyclic aromatic hydrocarbon 9,19-dihydrodinaphtho[3,2,1-
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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