80522-42-5

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TRIISOPROPYLSILYLTRIFLUOROMETHANESULFONATE

Product Code: SIT8387.0

Cas No: 80522-42-5

R&D quantities:

50 g
$270.00
10 g
$69.00
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
  • More reactive than SIT8384.0
  • Used to make Tsoc, (triisopropylsilyloxycarbonyl) protecting groups for amines
  • Steric bulk allows for selective silylation of compounds with more than one hydroxyl group
  • Summary of selective deprotection conditions is provided in Table 7 through Table 20 of the Silicon-Based Blocking Agents brochure
  • 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

    Formula: C10H21F3O3SSi

    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