PHENYLETHYNYLTRIMETHYLSILANE

Product Code: SIP6736.0
CAS No: 2170-06-1
SDS Sheets: EU | US
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Quantity
Price
 
5 g
$40.00
25 g
$159.00

Product data and descriptions listed are typical values, not intended to be used as specification.

  • HMIS

    2-2-1-X
  • Molecular Formula

    C11H14Si
  • Molecular Weight (g/mol)

    174.32
  • TSCA

    No
  • Boiling Point (˚C/mmHg)

    67/5
  • Density (g/mL)

    0.896
  • Flash Point (˚C)

    82 °C
  • Refractive Index @ 20˚C

    1.5284

Additional Properties

  • Hydrolytic Sensitivity

    1: no significant reaction with aqueous systems
  • 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.

    Safety

  • Packaging Under

    Nitrogen
  • 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
  • Silicon Chemistry, Articles

    Silicon-Based Formation of Carbon-Carbon Bonds – Larson

    Hatanaka and Hiyama first reported the palladium-catalyzed, fluoride-promoted reaction of aryl, alkenyl, allyl, and ethynyltrimethylsilanes with aryl, vinil and allyl halides to form the respective cross-coupled products

    Articles

    Some Aspects of the Chemistry of Alkynylsilanes – Larson

    In amongst the considerable chemistry of acetylenes there lies some unique chemistry of alkynylsilanes (silylacetylenes) some of which is reviewed herein. This unique character is exemplified not only in the silyl protection of the terminal C–H of acetylenes, but also in the ability of the silyl group to be converted into other functionalities after reaction of the alkynylsilane and to its ability to dictate and improve the regioselectivity of reactions at the triple bond. This, when combined with the possible subsequent transformations of the silyl group, makes their chemistry highly versatile and useful.