PHENYLDIMETHYLSILANE

Product Code: SIP6729.0
CAS No: 766-77-8
SDS Sheets: EU | US
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25 g
$200.00
100 g
$259.00
2 kg
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15 kg
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Prices listed are EXW price (Morrisville, PA US) in USD. Prices vary depending on currency and Incoterms.

Product data and descriptions listed are typical values, not intended to be used as specification.

  • Einecs Number

    212-170-5
  • Synonyms

    DIMETHYLPHENYLSILANE
  • HMIS

    2-2-1-X
  • Molecular Formula

    C8H12Si
  • Molecular Weight (g/mol)

    136.27
  • Purity (%)

    97%
  • TSCA

    Yes
  • Boiling Point (˚C/mmHg)

    156-157
  • Density (g/mL)

    0.889
  • Flash Point (˚C)

    38 °C
  • Melting Point (˚C)

    -124°
  • Refractive Index @ 20˚C

    1.4995

Additional Properties

  • Hydrolytic Sensitivity

    3: reacts with aqueous base

    • 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.

    Safety

  • Packaging Under

    Nitrogen

    • 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

    • 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.