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: 250
Dipole moment: 0.75 debye
Surface tension: 20.7 mN/m
?Hcomb: -1,272 kcal/mole
?Hform: -41 kcal/mole
Vapor pressure, 20°: 40 mm