766-77-8

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PHENYLDIMETHYLSILANE

Product Code: SIP6729.0

Cas No: 766-77-8

R&D quantities:

100 g
$187.00
25 g
$59.00
Phenyl-Containing Blocking Agent

Used as a protecting group for reactive hydrogens in alcohols, amines, thiols, and carboxylic acids. Organosilanes are hydrogen-like, can be introduced in high yield, and can be removed under selective conditions. They are stable over a wide range of reaction conditions and can be removed in the presence of other functional groups, including other protecting groups. The tolerance of silylated alcohols to chemical transformations summary is presented in Table 1 of the Silicon-Based Blocking Agents brochure.

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.

Phenyldimethylsilane; Dimethylphenylsilane;
  • Vapor pressure, 25 °C: 4 mm
  • Reacts with alcohols in presence of Wilkinson’s catalyst
  • Used to prepare α-phenyldimethylsilyl esters with high enantioselectivity
  • Yields optically active reduction products with chiral Rh or Pd catalysts
  • Undergoes 1,4-addition to pyridines forming N-silylated dihydropyridines
  • Used in the fluoride ion-catalyzed reduction of aldehydes and ketones, and α-substituted alkanones to threo products
  • Hydrosilylation of 1,4-bis(trimethylsilyl)butadiyne can go to the trisilyl allene or the trisilyl enyne
  • Erythro reduction of α-substituted alkanones to diols and aminoethanols
  • Used to reduce α-amino ketones to aminoethanols with high stereoselectivity
  • Together with CuCl reduces aryl ketones, but not dialkyl ketones
  • Used in the silylformylation of acetylenes
  • Excellent reducing agent for the reduction of enones to saturated ketones
  • Shows better selectivity than LAH in the reduction of oximes to alkoxyamines.
  • Extensive review of silicon based reducing agents: Larson, G.; Fry, J. L. "Ionic and Organometallic-Catalyzed Organosilane Reductions", Wipf, P., Ed.; Wiley, 2007
  • Summary of selective deprotection conditions is provided in Table 7 through Table 20 of the Silicon-Based Blocking Agents brochure
  • Boiling Point: 156-7°

    EINECS Number: 212-170-5

    Melting Point: -124°

    Molecular Weight: 136.27

    Alternative Name: DIMETHYLPHENYLSILANE

    Specific Gravity: 0.889

    Flashpoint: 38°C (100°F)

    HMIS Key: 2-2-1-X

    Hydrolytic Sensitivity: 3: reacts with aqueous base

    Formula: C8H12Si

    Refractive Index: 1.4995

    TSCA: TSCA

    Application: Review of synthetic utility.1
    Used to prepare ?-phenyldimethylsilyl esters with high enantioselectivity.2
    Yields optically active reduction products with chiral Rh or Pd catalysts.3
    Undergoes 1,4-addition to pyridines forming N-silylated dihydropyridines.4
    Hydrosilylation of 1,4-bis(trimethylsilyl)butadiyne can go to the trisilyl allene or the trisilyl enyne.5

    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. 254-255.
    2. Zhang, Y.-Z. et al. Angew. Chem., Int. Ed. Engl. 2008, 47, 8496.
    3. F&F: Vol. 12, p 209; Vol. 13, p 123; Vol. 15, p 168.
    4. Gutsulyak, D. V. et al. Angew. Chem., Int. Ed. Engl. 2011, 50, 1384.
    5. Kusumoto, T. et al. Bull. Chem. Soc. Jpn. 1992, 65, 1280.

    Additional Properties: Vapor pressure, 25°: 4 mm