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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.
Dimethylchlorosilane; Chlorodimethylsilane; Dimethylsilyl chloride
EINECS Number: 213-912-0
Specific Gravity: 0.868
Flashpoint: -25°C (-13°F)
HMIS Key: 3-4-2-X
Hydrolytic Sensitivity: 8: reacts rapidly with moisture, water, protic solvents
Refractive Index: 1.3827
Application: Review of synthetic utility.1
Enantioselectively converts ?-hydroxyketones to 1,2-diols.2
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. 156-157.
2. Burk, M. J.; Feaster, J. E. Tetrahedron Lett. 1992, 33, 2099.
Additional Properties: Surface tension: 17.1 mN/m202°?Hvap: 6.27 kcal/moleSpecific heat: 0.27 cal/g/°Thermal conductivity: 0.116 W/m°KUndergoes hydrosilylation reactions