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79271-56-0

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TRIETHYLSILYLTRIFLUOROMETHANESULFONATE

Product Code: SIT8335.0

Cas No: 79271-56-0

R&D quantities:

2.5 kg
$2,772.50
50 g
$198.00
10 g
$61.00
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.

Triethylsilyltrifluoromethanesulfonate; TES-OTf; Triethylsilyltriflate; Triethylsilyl trifluoromethanesulphonate; Trifluoromethanesulfonic acid triethylsilyl ester
  • More reactive than SIT8250.0
  • Useful for more hindered alcohols
  • Used primarily for the protection of alcohols
  • Can be used to protect amines and carboxylic acids
  • Summary of selective deprotection conditions is provided in Table 7 through Table 20 of the Silicon-Based Blocking Agents brochure
  • Boiling Point: 85-6° / 12

    EINECS Number: 279-124-4

    Molecular Weight: 264.34

    Specific Gravity: 1.169

    Flashpoint: 72°C (162°F)

    HMIS Key: 4-2-1-X

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

    Formula: C7H15F3O3SSi

    Refractive Index: 1.3892

    Application: Review of synthetic utility.1
    Triethylsilylation reagent.2
    Review on organosilane protecting groups.3
    In combination with lutidine selectively converts acetals to aldehydes without affecting silyl ethers.4
    Reacts with esters to form both the silyl ketene acetal and the ?-triethylsilyl ester.5

    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. 517-518.
    2. Emde, H. et al. Synthesis 1982, 1.
    3. Larson, G. L. “Silicon-Based Blocking Agents” Gelest, Inc. 2014.
    4. Fujioka, H. et al. J. Am. Chem. Soc. 2006, 128, 5930.
    5. Emde, H. et al. Liebigs Ann. Chem.1981, 1643.