TRIETHYLSILANE, 98%

Product Code: SIT8330.0
CAS No: 617-86-7
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Product data and descriptions listed are typical values, not intended to be used as specification.

  • Einecs Number

    210-535-3
  • HMIS

    2-4-1-X
  • Molecular Formula

    C6H16Si
  • Molecular Weight (g/mol)

    116.28
  • Purity (%)

    98%
  • TSCA

    Yes
  • Autoignition Temp (˚C)

    250
  • Boiling Point (˚C/mmHg)

    107-108
  • Density (g/mL)

    0.7309
  • Flash Point (˚C)

    -3
  • Melting Point (˚C)

    -157°
  • Refractive Index @ 20˚C

    1.4123
  • Viscosity at 25 ˚C (cSt)

    4.9

Additional Properties

  • Hydrolytic Sensitivity

    3: reacts with aqueous base
  • Surface Tension (mN/m)

    20.7

    • Application

    Versatile reducing agent; key reviews.1,2,3,4
    Employed in the regioselective reduction of a ketal in the synthesis of Tamiflu.10
    Review on organosilane protecting groups.5
    Silylates tertiary alcohols in presence of tris(pentafluorophenyl)borane.6
    Silylates arenes in presence of Ru catalyst and t-butylethylene.7
    Used in reductive cyclization of ynals.8
    Readily converted directly to triethylsilyl carboxylates.9

    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. 506-514.
    10. Federspiel, M. et al. Org. Proc. Res. Dev. 1999, 3, 266.
    2. Nagai, Y. Org. Prep. Proc. Int. 1980, 12, 13.
    3. F&F: Vol. 1, p 1218; Vol. 2, p 433; Vol. 3, p 304; Vol. 4, p 562; Vol. 6, p 652; Vol. 7, p 387; Vol. 8, p 501; Vol. 9, p 418; Vol. 10, p 483; Vol. 11, p 482; Vol. 15, p 338; Vol. 16, p 356; Vol. 17, p 367.
    4. Larson, G. L.; Fry, J. L. Ionic and Organometallic-Catalyzed Organosilane Reductions, Volume 71, Denmark, S. E., Ed. John WIley and Sons, 2008
    5. Larson, G. L. “Silicon-Based Blocking Agents” Gelest, Inc. 2014.
    6. Blackwell, J. M. et al. J. Org. Chem. 1999, 64, 4887.
    7. Ezbiansky, K. et al. J. Organometal. Chem. 1998, 17, 1455.
    8. Tang, X.-Q.; Montgomery, J. J. Am. Chem. Soc.1999, 121, 6098.
    9. Chahan, M. et al. Org. Lett. 2000, 2, 1027.

    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.

    Triethylsilane; Triethylsilyl hydride; Triethylsilicon hydride

  • Viscosity: 4.9 cSt
  • Dipole moment: 0.75 debye
  • Surface tension: 20.7 mN/m
  • ΔHform: -172 kJ/mol
  • ΔHcomb: -5,324 kJ/mol
  • Vapor pressure, 20 °: 40 mm
  • Silylates tertiary alcohols in presence of tris(pentafluorophenyl)borane
  • Silylates arenes in presence of Ru catalyst and t-butylethylene
  • Used in reductive cyclization of ynals
  • Readily converted directly to triethylsilyl carboxylates
  • Used to reduce metal salts
  • Enhances deprotection of t-butoxycarbonyl-protected amines and tert-butyl esters
  • Used in the reductive amidation of oxazolidinones with amino acids to provide dipeptides
  • Converts aldehydes to symmetrical and unsymmetrical ethers
  • Used in the ‘in-situ’ preparation of diborane and haloboranes
  • 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.