6999-19-5

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1-TRIMETHYLSILYLBUT-1-YNE-3-OL

Product Code: SIT8583.0

Cas No: 6999-19-5

R&D quantities:

10 g
$77.00
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.

1-Trimethylsilylbut-1-yne-3-ol; 3-Hydroxybutynyltrimethylsilane
  • Phosphate ester adds to α,β-unsaturated malonates
  • Useful in Sonogashira reactions to give substituted propargyl alcohols
  • 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: 82° / 35

    Molecular Weight: 142.27

    Specific Gravity: 0.85

    Flashpoint: 50°C (122°F)

    HMIS Key: 2-2-1-X

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

    Formula: C7H14OSi

    Refractive Index: 1.4449

    Application: Phosphate ester adds to ?,?-unsaturated malonates.1
    Useful in silicon-mediated Sonogashira cross-coupling reactions to give substituted propargyl alcohols.2

    Reference: 1. Song, Y. et al. Org. Lett. 2001, 3, 3543.
    2. Larson, G. L. “Silicon-Based Cross-Coupling Reagents” Gelest, Inc. 2011.

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