TRIMETHYLSILYL TRIFLUOROMETHANESULFONATE

Product Code: SIT8620.0
CAS No: 27607-77-8
SDS Sheets: EU | US
Pack Size
Quantity
Price
 
25 g
$50.00
100 g
$162.00
2.5 kg
$1,265.00
20 kg
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225 kg
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Product data and descriptions listed are typical values, not intended to be used as specification.

  • Einecs Number

    248-565-4
  • Synonyms

    TRIMETHYLSILYLTRIFLATE
  • HMIS

    3-2-1-X
  • Molecular Formula

    C4H9F3O3SSi
  • Molecular Weight (g/mol)

    222.25
  • TSCA

    Yes
  • Autoignition Temp (˚C)

    405
  • Boiling Point (˚C/mmHg)

    140-1°
  • Density (g/mL)

    1.225
  • Flash Point (˚C)

    40°C (104°F)
  • Refractive Index @ 20˚C

    1.360

Additional Properties

  • Hydrolytic Sensitivity

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

    Review of synthetic utility.1
    Review on organosilane protecting groups.2
    Reacts with ketones to form silyl enol ethers; Review.3
    Enhances the addition of terminal acetylenes to aldehydes.4
    Used in the nickel-catalyzed direct phenylation of C-H bonds in heteroaromatic system such as benzoxazoles.5

    Fieser

    F&F: Vol. 6, p 639; Vol. 8, p 497; Vol. 10, p 438; Vol. 11, p 584; Vol. 12, p 543; Vol. 13, p 118, p 149, p 187, p 321, p 329; Vol. 14, p 119, p 202, p 259, p 321, p 333; Vol. 15, p 66, p 102, p 108, p 346; Vol. 16, p 49, p 112, p 138, p 278, p 363; Vol. 17, p 26, p 379; Vol. 18, p 23, p 57, p 383; Vol. 20, p 408; Vol. 21, p 460.

    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. 518-537.
    2. Larson, G. L. “Silicon-Based Blocking Agents” Gelest, Inc. 2014.
    3. Simchen, G. In Advances in Silicon Chemistry; Larson, G., Ed.; JAI Press: Greenwich, Co, 1991; Vol. 1, p189.
    4. Downey, C. W. et al. J. Org. Chem. 2009, 74, 2904.
    5. Hachilya, H. et al. Angew. Chem., Int. Ed. Engl. 2010, 49, 2202.

    Safety

  • Packaging Under

    Nitrogen
  • Trimethylsilyl 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.

    Trimethylsilyltrifluoromethanesulfonate; Trimethylsilyltriflate; TMSOTf

  • Strong silylating agent for C- or O-silylations
  • Reacts with nitroalkanes to give N,N-bis(trimethylsiloxy)enamines
  • Nafion SAC-13 has been shown to be a recyclable catalyst for the trimethylsilylation of primary, secondary, and tertiary alcohols in excellent yields and short reaction times
  • Summary of selective deprotection conditions is provided in Table 7 through Table 20 of the Silicon-Based Blocking Agents brochure