2170-06-1

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PHENYLETHYNYLTRIMETHYLSILANE

Product Code: SIP6736.0

Cas No: 2170-06-1

R&D quantities:

25 g
$132.00
5 g
$33.00

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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.

Phenylethynyltrimethylsilane; Trimethylsilylphenylacetylene
  • Useful in trimethylsilyl-mediated Sonogashira reactions
  • Arylethynylsilanes react with propargyl chlorides to form 1,2- diene-4-ynes
  • Ethynylsilanes react with propargyl halides to form 1,4-diynes
  • Reacts with tetraphenylcyclopentadienone to form pentaphenylphenyltrimethylsilane
  • Cross couples with aryl halides and triflates as well as homocouples to 1,2-diynes
  • Undergoes alkynyl cross metathesis reactions
  • Provides the ethynyl silver acetylide
  • 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: 67° / 5

    Molecular Weight: 174.32

    Specific Gravity: 0.896

    Flashpoint: 82°C (180°F)

    HMIS Key: 2-2-1-X

    Hydrolytic Sensitivity: 1: no significant reaction with aqueous systems

    Formula: C11H14Si

    Refractive Index: 1.5284

    Application: Reacts with tetraphenylcyclopentadienone to form pentaphenylphenyltrimethylsilane.1
    Cross couples with aryl halides and triflates as well as homocouples to 1,2-diynes.2
    Undergoes alkynyl cross metathesis reactions.3
    Provides the ethynyl silver acetylide.4
    Reacts w/ propargyl chlorides to form 1,2-diene-4-ynes.5
    Ethynylsilanes react w/ propargyl halides to form 1,4-diynes.6

    Reference: 1. Jianhua, C. et al. In Silicon Chemistry; Corey, J., et al. Ed.; Wiley: 1988: p. 105.
    2. Nashihara, Y. et al. J. Org. Chem. 2000, 65, 1780.
    3. Furstner, A.; Mathes, C. Org. Lett. 2001, 3, 221.
    4. Vitérisi, A. et al. Tetrahedron Lett. 2006, 47, 2779.
    5. Montel, F. et al. Org. Lett. 2006, 8, 1905.
    6. Kuninobu, Y.; Ishii, E.; Takai, K. Angew. Chem., Int. Ed. Engl. 2007, 46, 3296.

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