789-25-3

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TRIPHENYLSILANE

Product Code: SIT8665.0

Cas No: 789-25-3

R&D quantities:

100 g
$234.00
25 g
$72.00
Tri-substituted Silane Reducing Agent

Organosilanes are hydrocarbon-like and possess the ability to serve as both ionic and free-radical reducing agents. These reagents and their reaction by-products are safer and more easily handled and disposed than many other reducing agents. The metallic nature of silicon and its low electronegativity relative to hydrogen lead to polarization of the Si-H bond yielding a hydridic hydrogen and a milder reducing agent compared to aluminum-, boron-, and other metal-based hydrides. A summary of some key silane reductions are presented in Table 1 of the Silicon-Based Reducing Agents brochure.

Triphenylsilane; Triphenylsilanlyl hydride
  • More effective radical-based reagent for reduction of organic halides than the trialkylsilanes
  • Compares well with tri-n-butyltin hydride in reduction of enones to ketones
  • Shows good selectivity in the reduction of cyclic hemiacetals
  • Converts O-acetyl furanoses and pyranoses to deoxy sugars
  • Extensive review of silicon based reducing agents: Larson, G.; Fry, J. L. "Ionic and Organometallic-Catalyzed Organosilane Reductions", Wipf, P., Ed.; Wiley, 2007
  • Boiling Point: 160-5° / 3

    EINECS Number: 212-333-0

    Melting Point: 42-4°

    Molecular Weight: 260.41

    Flashpoint: >200°C (>392°F)

    HMIS Key: 2-1-1-X

    Hydrolytic Sensitivity: 3: reacts with aqueous base

    Formula: C18H16Si

    Refractive Index: 1.6160

    TSCA: TSCA

    Application: Review of synthetic utility.1
    In presence of di-t-butylperoxide reduces esters to hydrocarbons.2
    Undergoes dehydrogenative coupling with alcohols.2

    Reference: 1. Handbook of Reagents for Organic Synthesis, Reagents for Silicon-Mediated Organic Synthesis, Fuchs, P. L. Ed., John Wiley and Sons, Ltd., 2011, p. 733-739.
    2. Sano, H. et al. Chem. Lett. 1986, 77.
    3. Yamanoi, Y. J. Org. Chem. 2005, 70, 9607.

    Fieser: F&F: Vol. 12, p 209; Vol. 13, p 334.