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Trialkylsilyl 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.
Triethylsilyltrifluoromethanesulfonate; TES-OTf; Triethylsilyltriflate; Triethylsilyl trifluoromethanesulphonate; Trifluoromethanesulfonic acid triethylsilyl ester
Boiling Point: 85-6° / 12
EINECS Number: 279-124-4
Molecular Weight: 264.34
Specific Gravity: 1.169
Flashpoint: 72°C (162°F)
HMIS Key: 4-2-1-X
Hydrolytic Sensitivity: 8: reacts rapidly with moisture, water, protic solvents
Refractive Index: 1.3892
Application: Review of synthetic utility.1
Review on organosilane protecting groups.3
In combination with lutidine selectively converts acetals to aldehydes without affecting silyl ethers.4
Reacts with esters to form both the silyl ketene acetal and the ?-triethylsilyl ester.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. 517-518.
2. Emde, H. et al. Synthesis 1982, 1.
3. Larson, G. L. “Silicon-Based Blocking Agents” Gelest, Inc. 2014.
4. Fujioka, H. et al. J. Am. Chem. Soc. 2006, 128, 5930.
5. Emde, H. et al. Liebigs Ann. Chem.1981, 1643.