998-30-1

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TRIETHOXYSILANE

Product Code: SIT8185.0

Cas No: 998-30-1

R&D quantities:

100 g
$143.00
25 g
$44.00
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.

Triethoxysilane; Silicon triethoxide; Triethoxysilylhydride
  • CAUTION: VAPORS CAUSE BLINDNESS — GOGGLES MUST BE WORN

  • DISPROPORTIONATES IN PRESENCE OF BASE TO PYROPHORIC PRODUCTS

  • Contains trace Si–Cl for stability
  • ΔHcomb: -4,604 kJ/mol
  • ΔHform: 925 kJ/mol
  • ΔHvap: 175.4 kJ/mol
  • Surface tension: 22.3 mN/m
  • Vapor pressure, 20 °C: 20.2 mm
  • Critical temperature: 244 °C
  • Dipole moment: 1.78 debye
  • Hydrosilylates olefins in presence of Pt
  • Used to convert alkynes to (E)–alkenes via hydrosilylation-desilylation
  • Reduces amides to amines in the presence of Zn(OAc)2
  • Used in the reduction of phosphine oxides to phosphines
  • Reduces esters in the presence of zinc hydride catalyst
  • Reduces aldehydes and ketones to alcohols via the silyl ethers in presence of fluoride ion
  • Gives 1,2 reduction of enones to allyl alcohols
  • Extensive review of silicon based reducing agents: Larson, G.; Fry, J. L. "Ionic and Organometallic-Catalyzed Organosilane Reductions", Wipf, P., Ed.; Wiley, 2007
  • Boiling Point: 131-2°

    EINECS Number: 213-650-7

    Melting Point: -170°

    Molecular Weight: 164.28

    Specific Gravity: 0.8753

    Flashpoint: 26°C (79°F)

    HMIS Key: 4-3-1-X

    Hydrolytic Sensitivity: 7: reacts slowly with moisture/water

    Formula: C6H16O3Si

    Refractive Index: 1.3767

    TSCA: TSCA

    Application: Review of synthetic utility.1
    Reducing agent.2
    Used to convert alkynes to (E)-alkenes via hydrosilylation-desilylation.3
    Reduces amides to amines in the presence of Zn(OAc)2.4
    Used in the reduction of phosphine oxides to phosphines.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. 501-505.
    2. Boyer, J. et al. Synthesis 1981, 558.
    3. Trost, B. M. et al. J. Am. Chem. Soc. 2002, 124, 7922.
    4. Dos, S. et al. J. Am. Chem. Soc. 2010, 132, 1770.
    5. Coumbe, T. et al. Tetrahedron Lett. 1994, 35, 625.

    Fieser:

    Additional Properties: Dipole moment: 1.78 debye
    Surface tension: 22.3 mN/m
    ?Hcomb: -1,100 kcal/mole
    Critical temperature: 244°C
    ?Hform: 221 kcal/mole
    ?Hvap: 41.9 kcal/mole
    Contains trace Si-Cl for stability
    Hydrosilylates olefins in presence of Pt
    Vapor pressure, 20°: 20.2 mm
    Viscosity: 0.6 cSt