Skip to Content
Merck
All Photos(3)

Documents

360031

Sigma-Aldrich

(Triisopropylsilyl)acetylene

97%

Synonym(s):

Ethynyltriisopropylsilane

Sign Into View Organizational & Contract Pricing
All Photos(3)

About This Item

Linear Formula:
[(CH3)2CH]3SiC≡CH
CAS Number:
89343-06-6
Molecular Weight:
182.38
Beilstein:
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

Looking for similar products? Visit Product Comparison Guide

Related Categories

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

Signal Word

Warning

Hazard Statements

H226,H315,H319,H335

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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 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.
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)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service