DIPHENYLSILANE

Product Code: SID4559.0
CAS No: 775-12-2
SDS Sheets: EU | US
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25 g
$100.00
100 g
$323.00
2 kg
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Product data and descriptions listed are typical values, not intended to be used as specification.

  • HMIS

    2-1-1-X
  • Molecular Formula

    C12H12Si
  • Molecular Weight (g/mol)

    184.31
  • Purity (%)

    97%
  • TSCA

    Yes
  • Boiling Point (˚C/mmHg)

    95-7° / 13
  • Density (g/mL)

    0.9969
  • Flash Point (˚C)

    98 °C
  • Refractive Index @ 20˚C

    1.5795

Additional Properties

  • Hydrolytic Sensitivity

    3: reacts with aqueous base

    • Application

    Converts amides to aldehydes in combination with Ti(OiPr)4.2
    Selective reduction of esters.3
    Silylates 1,2-diols in presence of tris(pentafluorophenyl)borane.4
    Used in enantioselective reduction of imines.5
    Reducing agent.1

    Fieser

    F&F: Vol. 1, p 348.

    Reference

    2. Bower, S. et al. Angew. Chem., Int. Ed. Engl. 1996, 35, 1515.
    3. Onta, T. et al. Tetrahedron Lett. 1999, 40, 6963.
    4. Blackwell, J. M. et al. J. Org. Chem. 1999, 64, 4887.
    5. Takai, I. et al. Organometallics 1999, 18, 2271.

    Safety

  • Packaging Under

    Nitrogen

    • Dialkyl 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.

    Diphenylsilane; Dihydridodiphenylsilane

  • Converts amides to aldehydes in combination with Ti(OiPr)4
  • Used in the preparation of silyl-substituted alkylidene complexes of tantalum
  • Used in the ionic reduction of enones to saturated ketones
  • Used in the reductive cyclization of unsaturated ketones
  • Reduces esters in the presence of zinc hydride catalyst
  • Silylates 1,2-diols in presence of tris(pentafluorophenyl)borane
  • Reduces α-halo ketones in presence of Mo(0)
  • Used in enantioselective reduction of imines
  • Reduces thio esters to ethers
  • Selective reduction of esters
  • Reduces esters to alcohols with Rh catalysis
  • Employed in the asymmetric reduction of methyl ketones and other ketones
  • Reductively cleaves allyl acetates
  • 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

    Tetramethyldisiloxane: A Practical Organosilane Reducing Agent – Larson

    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.