t-BUTYLDIMETHYLSILYLTRIFLUOROMETHANESULFONATE

Product Code: SIB1967.0
CAS No: 69739-34-0
SDS Sheets: EU | US
Pack Size
Quantity
Price
 
10 g
$81.00
50 g
$319.00
2 kg
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20 kg
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Product data and descriptions listed are typical values, not intended to be used as specification.

  • Einecs Number

    274-102-0
  • HMIS

    3-3-1-X
  • Molecular Formula

    C7H15F3O3SSi
  • Molecular Weight (g/mol)

    264.33
  • Boiling Point (˚C/mmHg)

    65° / 10
  • Density (g/mL)

    1.151
  • Flash Point (˚C)

    36°C (97°F)
  • Refractive Index @ 20˚C

    1.3848

Additional Properties

  • Hydrolytic Sensitivity

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

    Review of synthetic utility.1
    Powerful silylation reagent and Lewis acid.2
    Excellent promoter for gylcosidations, especially for trichloroacetimidates.3

    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. 127-135.
    2. Review: Simchen, G. Advances in Silicon Chemistry; JAI Press: Greenwich, Co, 1991; Larson, G. L. Ed., Vol. 1, 189.
    3. Roush, W. R. et al. Org. Lett. 1999, 1, 891; and Roush, W. R.; Narayan, S. Org. Lett. 1999, 1, 899.

    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.

    tert-Butyldimethylsilyltrifluoromethanesulfonate; TBS-OTf; t-Butyldimethylsilyltriflate

  • More reactive than SIB1935.0
  • Converts acetates to TBS ethers
  • Used for the protection of alcohols, amines, thiols, lactams, and carboxylic acids
  • Clean NMR characteristics of protecting group
  • Facile removal with flouride ion sources
  • Summary of selective deprotection conditions is provided in Table 7 through Table 20 of the Silicon-Based Blocking Agents brochure