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TRIETHYLSILYLTRIFLUOROMETHANESULFONATE
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
Formula: C7H15F3O3SSi
Refractive Index: 1.3892
Application: Review of synthetic utility.1
Triethylsilylation reagent.2
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.
Silanes
Bulk Metal-Organics and Silanes: Pharmaceutical & Organic Synthesis
Silicon-Based Blocking Agents
Enabling Synthetic Organic Transformations