69739-34-0

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t-BUTYLDIMETHYLSILYLTRIFLUOROMETHANESULFONATE

Product Code: SIB1967.0

Cas No: 69739-34-0

R&D quantities:

50 g
$319.00
10 g
$81.00
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.

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
  • Boiling Point: 65° / 10

    EINECS Number: 274-102-0

    Molecular Weight: 264.33

    Specific Gravity: 1.151

    Flashpoint: 36°C (97°F)

    HMIS Key: 3-3-1-X

    Hydrolytic Sensitivity: 8: reacts rapidly with moisture, water, protic solvents

    Formula: C7H15F3O3SSi

    Refractive Index: 1.3848

    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.

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