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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
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
Refractive Index: 1.3767
Application: Review of synthetic utility.1
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.
Additional Properties: Dipole moment: 1.78 debyeSurface tension: 22.3 mN/m?Hcomb: -1,100 kcal/moleCritical temperature: 244°C?Hform: 221 kcal/mole?Hvap: 41.9 kcal/moleContains trace Si-Cl for stabilityHydrosilylates olefins in presence of PtVapor pressure, 20°: 20.2 mmViscosity: 0.6 cSt