Additional Properties
- 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 °C
- Melting Point (˚C) -157°
- Refractive Index @ 20˚C 1.4123
- Viscosity at 25 ˚C (cSt) 4.9
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
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
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
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.
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