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360031

(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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24862139
MDL number:
MFCD00075452
Beilstein/REAXYS Number:
3536241
Assay:
97%
Form:
liquid
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Quality Segment

100

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

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

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

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