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Boiling Point: 140-1°
EINECS Number: 248-565-4
Molecular Weight: 222.25
Alternative Name: TRIMETHYLSILYLTRIFLATE
Specific Gravity: 1.225
Flashpoint: 40°C (104°F)
HMIS Key: 3-2-1-X
Hydrolytic Sensitivity: 8: reacts rapidly with moisture, water, protic solvents
Refractive Index: 1.360
Application: Review of synthetic utility.1
Review on organosilane protecting groups.2
Reacts with ketones to form silyl enol ethers; Review.3
Enhances the addition of terminal acetylenes to aldehydes.4
Used in the nickel-catalyzed direct phenylation of C-H bonds in heteroaromatic system such as benzoxazoles.5
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. 518-537.
2. Larson, G. L. “Silicon-Based Blocking Agents” Gelest, Inc. 2014.
3. Simchen, G. In Advances in Silicon Chemistry; Larson, G., Ed.; JAI Press: Greenwich, Co, 1991; Vol. 1, p189.
4. Downey, C. W. et al. J. Org. Chem. 2009, 74, 2904.
5. Hachilya, H. et al. Angew. Chem., Int. Ed. Engl. 2010, 49, 2202.
Fieser: F&F: Vol. 6, p 639; Vol. 8, p 497; Vol. 10, p 438; Vol. 11, p 584; Vol. 12, p 543; Vol. 13, p 118, p 149, p 187, p 321, p 329; Vol. 14, p 119, p 202, p 259, p 321, p 333; Vol. 15, p 66, p 102, p 108, p 346; Vol. 16, p 49, p 112, p 138, p 278, p 363; Vol. 17, p 26, p 379; Vol. 18, p 23, p 57, p 383; Vol. 20, p 408; Vol. 21, p 460.
Additional Properties: 405Vapor pressure, 26°: 14 mm