2170-06-1

All structures are computer generated. Please rely on the product data below for placing your order. If you see any errors in structures, please email customer service so that they can be addressed.

PHENYLETHYNYLTRIMETHYLSILANE

Product Code: SIP6736.0

Cas No: 2170-06-1

25 g
$132.00
5 g
$33.00
Save for Later
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

    • 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.

    Fieser: