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Trimethylsilyl Blocking Agent
Used as a protecting group for reactive hydrogens in alcohols, amines, thiols, and carboxylic acids. Organosilanes are hydrogen-like, can be introduced in high yield, and can be removed under selective conditions. They are stable over a wide range of reaction conditions and can be removed in the presence of other functional groups, including other protecting groups. The tolerance of silylated alcohols to chemical transformations summary is presented in Table 1 of the Silicon-Based Blocking Agents brochure.
Trimethylsilyltrifluoromethanesulfonate; Trimethylsilyltriflate; TMSOTf
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