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EINECS Number: 217-007-1
Specific Gravity: 0.884
Flashpoint: -5°C (23°F)
HMIS Key: 3-4-1-X
Hydrolytic Sensitivity: 8: reacts rapidly with moisture, water, protic solvents
Refractive Index: 1.4137
Application: Review of synthetic utility.1
Used in synthesis of highly substituted unsaturated alcohols.2
Reductively cross-couples with allyl alcohols to form butenols after oxidation.3
Used to silylate unsaturated alcohols, which can be RCM-cyclized to a vinylsilyl ether, which in turn can be subjected to a silicon-based cross-coupling.4
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. 157-161.
2. Denmark, S. E.; Lang, S. M. Org. Lett. 2001, 3, 1749.
3. Belardi J. K.; Micalizio, G. C. J. Am. Chem. Soc. 2008, 130, 16870.
4. Denmark, S. E.; Yang, S.-M. Org. Lett. 2003, 3, 1749.