1777-03-3

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ETHYNYLTRIETHYLSILANE

Product Code: SIE4902.0

Cas No: 1777-03-3

R&D quantities:

5 g
$108.00
Alkynylsilane Cross-Coupling Agent

The cross-coupling reaction is a highly useful methodology for the formation of carbon-carbon bonds. It involves two reagents, with one typically being a suitable organometallic reagent - the nucleophile - and the other a suitable organic substrate, normally an unsaturated halide, tosylate or similar - the electrophile.

Ethynyltriethylsilane; Triethylsilylacetylene
  • More stable protected acetylene useful in Sonogashira reactions.
  • Reacts with enol silyl ethers to form α,α-bis-trans-&beta-triethylsilylethenyl ketones
  • Extensive review of silicon based cross-coupling agents: Denmark, S. E. et al. "Organic Reactions, Volume 75" Denmark, S. E. ed., John Wiley and Sons, 233, 2011
  • Boiling Point: 136°

    Molecular Weight: 140.30

    Alternative Name: TRIETHYLSILYLACETYLENE

    Specific Gravity: 0.783

    Flashpoint: 17°C (63°F)

    HMIS Key: 2-4-1-X

    Hydrolytic Sensitivity: 4: no reaction with water under neutral conditions

    Formula: C8H16Si

    Refractive Index: 1.4430

    Application: Reacts with enol silyl ethers to form ?,?-bis-trans-?-triethylsilylethenyl ketones.1
    Useful in Sonogashira cross-coupling reactions w/ more stable silyl group than the trimethylsilyl group.2

    Reference: 1. Amemiya, R. et al. Tetrahedron Lett. 2006, 47, 1797.
    2. Larson, G. L. “Silicon-Based Cross-Coupling Reagents” Gelest, Inc. 2011.