TRIFLUOROMETHYLTRIMETHYLSILANE

Product Code: SIT8362.0
CAS No: 81290-20-2
SDS Sheets: EU | US
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25 g
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5 g
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17 kg
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2 kg
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Product data and descriptions listed are typical values, not intended to be used as specification.

  • Synonyms

    RUPPERT'S REAGENT
  • HMIS

    3-4-0-X
  • Molecular Formula

    C4H9F3Si
  • Molecular Weight (g/mol)

    142.20
  • Boiling Point (˚C/mmHg)

    55°
  • Density (g/mL)

    0.9626
  • Flash Point (˚C)

    -10°C (14°F)
  • Refractive Index @ 20˚C

    1.3304

Additional Properties

  • Hydrolytic Sensitivity

    4: no reaction with water under neutral conditions
  • Application

    Key reviews.1,2,3
    Silylates cyclopropenes to give cyclopropenyltrimethylsilanes.10
    Trifluoromethylates terminal acetylenes.11
    Gives trifluoromethylthiolation of terminal alkynes in the presence of sulfur.12
    Trifluoromethylates carbonyl compounds.4
    Converts esters to trifluoromethyl ketones.5
    Used to prepare trifluoromethyl vicinal ethylene diamines.6
    Used in a simple preparation of potassium (trifluoromethyl)trifluoroborate.7
    Used to prepare trifluoromethyltitanium complexes.8
    Trifluoromethylates aldehydes, ketones and imines in good yield.9

    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. 539-546.
    10. Fordyce, E. A. F. et al. J. Chem. Soc., Chem. Commun. 2008, 1124.
    11. Chu, L.; Qing, F.-L. J. Am. Chem. Soc. 2010, 132, 7262.
    12. Chen, C. et al. J. Am. Chem. Soc. 2012, 134, 12454.
    2. Prakash, G. et al. Chem. Rev. 1997, 97, 757.
    3. Singh, R. P.; Shreeve. J. M. Tetrahedron 2000, 56, 7613.
    4. Prakash, G. et al. J. Am. Chem. Soc. 1989, 111, 393.
    5. Singh, R. et al. J. Org. Chem. 1999, 64, 2873.
    6. Prakash, G. K. S.; Mandal, M. J. Am. Chem. Soc. 2002, 124, 6538.
    7. Molander, G. A.; Hoag, B. P. Organometallics 2003, 22, 3313.
    8. Taw, F. L. et al. J. Am. Chem. Soc. 2003, 125, 14712.
    9. Matsukawa, S.; Saijo, M. Tetrahedron Lett. 2008, 49, 4655.

    Safety

  • Packaging Under

    Nitrogen