COMMERCIAL
6224-91-5

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1-TRIMETHYLSILYLPROPYNE

Product Code: SIT8606.5

Cas No: 6224-91-5

R&D quantities:

25 g
$154.00
5 g
$39.00

Interested in a Commercial Order?

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.

1-Trimethylsilylpropyne; Propynyltrimethylsilane; 1-(Trimethylsilyl)prop-1-yne
  • Forms polymers with very high oxygen permeability
  • Useful in Sonogashira reactions
  • Polymerization catalyzed with TaCl5/(C6H5)3Bi
  • Converts aldehydes to 1,3-dienes in presence of Cp2Zr(H)Cl
  • Used in the preparation of alkynylxenon fluoride
  • Polymeric version available, SSP-070
  • 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: 99-100°

    EINECS Number: 228-314-5

    Melting Point: -69°

    Molecular Weight: 112.25

    Specific Gravity: 0.758

    Flashpoint: -3°C (27°F)

    HMIS Key: 2-4-0-X

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

    Formula: C6H12Si

    Refractive Index: 1.4091

    TSCA: TSCA

    Application: Forms polymers with very high oxygen permeability.1
    Polymerization catalyzed with TaCl5/(C6H5)3Bi.2
    Converts aldehydes to 1,3-dienes in presence of Cp2Zr(H)Cl.3
    Synthetic reagent.4
    Used in the preparation of alkynylxenon fluoride.5
    Useful in silicon-mediated Sonogashira cross-coupling reactions.6

    Reference: 1. Masuda, T. et al. J. Am. Chem. Soc. 1983, 105, 7473.
    2. Masuda, T. et al. J. Polym. Sci., Part A: Polym. Chem. 1987, 25, 1353.
    3. Maeta, H. et al. Tetrahedron Lett. 1992, 33, 5969.
    4. F&F: Vol. 2, p 239; Vol. 6, p 638.
    5. Schmidt, H. et al. Inorg. Chem. 2004, 43, 1837.
    6. Larson, G. L. “Silicon-Based Cross-Coupling Reagents” Gelest, Inc. 2011.