14630-40-1

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BIS(TRIMETHYLSILYL)ACETYLENE

Product Code: SIB1850.0

Cas No: 14630-40-1

R&D quantities:

10 g
$53.00
50 g
$209.00

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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.

Bis(trimethylsilyl)acetylene; Bis(trimethylsilyl)ethyne
  • Useful in Sonogashira cross-coupling reactions
  • Versatile reagent for introducing unsaturation
  • Used to prepare 1,2-bis(aryl)acetylenes
  • Reacts with internal acetylenes to form 1,2,4,5-tetrasubstituted benzenes
  • Used to prepare 4-alkynylthiazoles
  • 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: 133-5°

    EINECS Number: 238-671-9

    Melting Point: 22°

    Molecular Weight: 170.40

    Specific Gravity: 0.770

    Flashpoint: 2°C (36°F)

    HMIS Key: 2-4-1-X

    Hydrolytic Sensitivity: 2: reacts with aqueous acid

    Formula: C8H18Si2

    Refractive Index: 1.413

    TSCA: TSCA

    Application: Key review.1
    Key review.2
    Used to prepare 1,2-bis(aryl)acetylenes.3
    Reacts with internal acetylenes to form 1,2,4,5-tetrasubstituted benzenes.4
    Useful in silicon-mediated Sonogashira cross-coupling reactions.5
    Used to prepare 4-alkynylthiazoles.6

    Reference: 1. Weber, W. In Silicon Reagents for Organic Synthesis; Springer-Verlag: 1983, p129.
    2. Vollhardt, P. Acc. Chem. Res. 1977, 10, 1.
    3. Nishihara, Y. et al. J. Org. Chem. 2000, 65, 1780.
    4. Li, S. et al. Org. Lett. 2009, 11, 3318.
    5. Larson, G. L. “Silicon-Based Cross-Coupling Reagents” Gelest, Inc. 2011.
    6. Arunkukmar, K. et al. Tetrahedron Lett. 2012, 53, 3885.

    Fieser:

    Additional Properties: Versatile reagent for introducing unsaturation