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Key Documents

360031

Sigma-Aldrich

(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

Quality Level

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

Signal Word

Warning

Hazard 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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