TRIISOPROPYLSILYLTRIFLUOROMETHANESULFONATE

Product Code: SIT8387.0
CAS No: 80522-42-5
SDS Sheets: EU | US
Pack Size
Quantity
Price
 
10 g
$69.00
50 g
$270.00
2 kg
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18 kg
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Product data and descriptions listed are typical values, not intended to be used as specification.

  • HMIS

    3-1-1-X
  • Molecular Formula

    C10H21F3O3SSi
  • Molecular Weight (g/mol)

    306.41
  • Boiling Point (˚C/mmHg)

    45-6° / 0.03
  • Density (g/mL)

    1.136
  • Flash Point (˚C)

    100°C (212°F)
  • Refractive Index @ 20˚C

    1.4140

Additional Properties

  • Hydrolytic Sensitivity

    8: reacts rapidly with moisture, water, protic solvents
  • Application

    Review of synthetic utility.1,2

    Fieser

    F&F: Vol. 11, p 567; Vol. 13, p 11; Vol. 21, p 254.

    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.

    Safety

  • Packaging Under

    Nitrogen
  • 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