1,1,1-Trifluoroacetylacetone

1,1,1-Trifluoroacetylacetone

1,1,1-Trifluoroacetylacetone

Chemical compound

1,1,1-Trifluoroacetylacetone is the organofluorine compound with the formula CF3C(O)CH2C(O)CH3. It is a colorless liquid. Like other 1,3-diketones, it is used as a precursor to heterocycles, e.g. pyrazoles, and metal chelates.[1] It is prepared by condensation of esters of trifluoroacetic acid with acetone.[2]

Quick Facts Names, Identifiers ...

According to an analysis by proton NMR spectroscopy, the compound exists predominantly (97% at 33 °C, neat) as the enol. For comparison under the same conditions, the percent enol for acetylacetone and hexafluoroacetylacetone are 85 and 100%, respectively.[3]

References

  1. [1]
    Morris, M. L.; Moshier, Ross W.; Sievers, Robert E. (1967). "Tetrakis(1,1,1-trifluoro-2,4-pentanedionato)zirconium(and Hafnium)". Inorganic Syntheses. Vol. 9. pp. 50–52. doi:10.1002/9780470132401.ch15. ISBN 9780470132401.
  2. [2]
    Henne, Albert L.; Newman, Melvin S.; Quill, Laurence L.; Staniforth, Robert A. (1947). "Alkaline condensation of fluorinated esters with esters and ketones". Journal of the American Chemical Society. 69 (7): 1819–20. doi:10.1021/ja01199a075.
  3. [3]
    Jane L. Burdett; Max T. Rogers (1964). "Keto-Enol Tautomerism in β-Dicarbonyls Studied by Nuclear Magnetic Resonance Spectroscopy. I. Proton Chemical Shifts and Equilibrium Constants of Pure Compounds". J. Am. Chem. Soc. 86: 2105–2109. doi:10.1021/ja01065a003.
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