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360031 Sigma-Aldrich

(Triisopropylsilyl)acetylene

97%

Synonym: Ethynyltriisopropylsilane

  • CAS Number 89343-06-6

  • Linear Formula [(CH3)2CH]3SiC≡CH

  • Molecular Weight 182.38

  •  Beilstein/REAXYS Number 3536241

  •  MDL number MFCD00075452

  •  PubChem Substance ID 24862139

  •  NACRES NA.22

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Properties

Related Categories Alkynes, Building Blocks, Chemical Synthesis, Organic Building Blocks, Terminal More...
assay   97%
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

Description

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.

Packaging

5, 25 g in glass bottle

Safety & Documentation

Safety Information

Symbol 
Signal word 
Warning
Hazard statements 
Precautionary statements 
Target organs 
Respiratory system
RIDADR 
UN 1993C 3 / PGIII
WGK Germany 
WGK 3
Flash Point(F) 
132.8 °F - closed cup
Flash Point(C) 
56 °C - closed cup

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

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Peer-Reviewed Papers
15

References

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