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1066-54-2

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ETHYNYLTRIMETHYLSILANE, 98%

Product Code: SIE4904.0

Cas No: 1066-54-2

R&D quantities:

1.5 kg
$1,231.50
25 g
$160.00
5 g
$41.00
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.

Ethynyltrimethylsilane; Trimethylsilylacetylene
  • Vapor pressure, 20 °C: 214 mm
  • Useful in Sonogashira reactions with differentiated reactivity at each terminus leading to unsymmetrical diaryl acetylenes
  • Reacts with aryl aldehydes to give diethynylmethanes (1,4-diynes)
  • Doped polymer films are conductive
  • Ethynylates aromatic compounds
  • Precursor to trimethylsilylethynyl copper reagent
  • Lithiated derivative (n-BuLi treatment) reacts with halotriazines to produce monomers
  • Employed in ortho ethenylation of phenols
  • Undergoes Diels-Alder reactions with butadienes
  • Converts imines to propargyl amines
  • Forms propargylic amines from aldehydes and amines in aqueous system
  • Regioselectively forms either regioisomeric enyne upon addition to propargyl amines depending on catalyst employed
  • Reacts with aryl aldehydes to form diethynylmethane derivatives
  • Useful in the preparation of unsymmetrical diarylacetylenes
  • 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: 52°

    EINECS Number: 213-919-9

    Molecular Weight: 98.22

    Alternative Name: TRIMETHYLSILYLACETYLENE

    Specific Gravity: 0.709

    Flashpoint: -26°C (-15°F)

    HMIS Key: 2-4-1-X

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

    Formula: C5H10Si

    Purity: 98%

    Refractive Index: 1.3880

    TSCA: TSCA

    Application: Review of synthetic utility.1
    Reacts w/ aryl aldehydes to form diethynylmethane derivatives.10
    Useful in the preparation of unsymmetrical diarylacetylenes.11
    Ethynylates aromatic compounds.2
    Precursor to trimethylsilylethynyl copper reagent.3
    Lithiated derivative (n-BuLi treatment) reacts with halotriazines to produce monomers.4
    Employed in ortho ethenylation of phenols.5
    Undergoes Diels-Alder reactions with butadienes.6
    Converts imines to propargyl amines.7
    Forms propargylic amines from aldehydes and amines in aqueous system.8
    Regioselectively forms either regioisomeric enyne upon addition to propargyl amines depending on catalyst employed.9

    Reference: 1. Handbook of Reagents for Organic Synthesis, Reagents for Silicon-Mediated Organic Synthesis, Fuchs, P. L. Ed., John Wiley and Sons, Ltd., 2011, p. 569-580.
    10. Girard, D. et al. Tetrahedron Lett. 2007, 48, 6022.
    11. Mio, M. et al. Org. Lett. 2002, 4, 3199.
    2. Austin, W. et al. J. Org. Chem. 1981, 46, 2280.
    3. Sakata, H. et al. Tetrahedron Lett. 1987, 28, 5719.
    4. Kouveetakis, J. et al. Chem. Mater. 1994, 6, 636.
    5. Kobayashi, K.; Yamaguchi, M. Org. Lett. 2001, 3, 241.
    6. Paik, S.-J. et al. Org. Lett. 1999, 1, 2045.
    7. Fischer, C.; Carreira, E. M. Org. Lett. 2001, 3, 4319.
    8. Wei, C.; Li, C.-J. J. Am. Chem. Soc. 2003, 125, 9584.
    9. Matsuyama, N. et al. J. Org. Chem. 2009, 74, 3576.

    Fieser:

    Additional Properties: 310
    Doped polymer films are conductive
    Vapor pressure, 20°: 214 mm