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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.
Triisopropylsilyltrifluoromethanesulfonate; Triisopropylsilyltriflate; TIPS-OTf
Boiling Point: 45-6° / 0.03
Molecular Weight: 306.41
Specific Gravity: 1.136
Flashpoint: 100°C (212°F)
HMIS Key: 3-1-1-X
Hydrolytic Sensitivity: 8: reacts rapidly with moisture, water, protic solvents
Refractive Index: 1.4140
Application: Review of synthetic utility.1,2
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. 559-562.
2. Rucker, C. Chem. Rev. 1995, 95, 1009.
Fieser: F&F: Vol. 11, p 567; Vol. 13, p 11; Vol. 21, p 254.
Additional Properties: Reactive form of TIPS protecting group