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25 g
$87.00
100 g
$281.00
2 kg
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Product data and descriptions listed are typical values, not intended to be used as specification.

  • Einecs Number

    212-333-0
  • HMIS

    2-1-1-X
  • Molecular Formula

    C18H16Si
  • Molecular Weight (g/mol)

    260.41
  • Purity (%)

    97%
  • TSCA

    Yes
  • Boiling Point (˚C/mmHg)

    160-165/3
  • Flash Point (˚C)

    >200 °C
  • Melting Point (˚C)

    42-4°
  • Refractive Index @ 20˚C

    1.6160

Additional Properties

  • Hydrolytic Sensitivity

    3: reacts with aqueous base
  • Application

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

    Fieser

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

    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.

    Safety

  • Packaging Under

    Nitrogen
  • 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
  • Silicon Chemistry, Articles

    Key Organosilane Reductions – Larson

    The Si-H bond, based on the relative electrongativities of Si and H, is polarised such that the hydrogen is slightly hydridic in nature. The fact that the silanes are not strongly hydridic makes them excellent candidates for mild and selective reductions of organic functional groups.

    Silicon Chemistry, Articles

    Organosilane Reductions with Polymethylhydrosiloxanes – Larson

    The reduction of a comprehensive range of organic functional groups ranging from carboxylic acids to aryl fluorides have been shown to be possible with a variety of organosilanes. A comprehensive review of the ionic and transition metal-catalyzed reductions of organic functional groups has recently appeared.

    Silicon Chemistry, Articles

    The Synthesis of Gliflozins – Larson

    Some of the general approaches to the key steps in the synthesis of gliflozins, a class of glucose transporters, are discussed. In particular the glycosidation step for the introduction of the key aryl moiety onto the glucose and the reduction steps are presented.  Click here for more product information on tetramethyldisiloxane (TMDO, TMDS) reducing agent.