5272-36-6

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3-TRIMETHYLSILYLPROPARGYL ALCOHOL

Product Code: SIT8604.0

Cas No: 5272-36-6

R&D quantities:

25 g
$374.00
5 g
$94.00
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.

3-Trimethylsilylpropargyl alcohol; 3-Trimethylsilyl-2-propyn-1-ol
  • Useful in Sonogashira reactions to give substituted propargyl alcohols
  • Hydromagnesiation of triple bond yields intermediates for terpene synthesis
  • 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: 170-2°

    EINECS Number: 226-094-5

    Molecular Weight: 128.25

    Alternative Name: 3-TRIMETHYLSILYL-2-PROPYN-1-OL

    Specific Gravity: 0.875

    Flashpoint: 65°C (149°F)

    HMIS Key: 3-2-0-X

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

    Formula: C6H12OSi

    Refractive Index: 1.4518

    TSCA: TSCA

    Application: Useful in silicon-mediated Sonogashira cross-coupling reactions to give substituted propargyl alcohols.1

    Reference: 1. Larson, G. L. “Silicon-Based Cross-Coupling Reagents” Gelest, Inc. 2011.

    Fieser: F&F: Vol. 10, p 70; Vol. 11, p 164.

    Additional Properties: Hydromagnesiation of triple bond yields intermediates for terpene synthesis