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TRIETHYLSILANE, 98%
Boiling Point: 107-8°
EINECS Number: 210-535-3
Melting Point: -157°
Molecular Weight: 116.28
Specific Gravity: 0.7309
Flashpoint: -3°C (27°F)
HMIS Key: 2-4-1-X
Hydrolytic Sensitivity: 3: reacts with aqueous base
Formula: C6H16Si
Purity: 98%
Refractive Index: 1.4123
TSCA: TSCA
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.
Fieser:
Additional Properties: 250Dipole moment: 0.75 debyeSurface tension: 20.7 mN/m?Hcomb: -1,272 kcal/mole?Hform: -41 kcal/moleVapor pressure, 20°: 40 mm
Metal-Organics
Metal-Organics
Key Organosilane Reductions – Larson
The Synthesis of Gliflozins – Larson
Organosilane Reductions with Polymethylhydrosiloxanes – Larson
Tetramethyldisiloxane: A Practical Organosilane Reducing Agent – Larson