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1,1,1-Trifluoroacetylacetone

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1,1,1-Trifluoroacetylacetone
Names
Preferred IUPAC name 1,1,1-Trifluoropentane-2,4-dione
Other names 1,1,1-Trifluoro-2,4-pentanedione, (trifluoroacetyl)acetone, 1,1,1-(trifluoroacetyl)acetone, 1,1,1-TFAA
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.006.090 Edit this at Wikidata
EC Number
  • 206-698-5
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C5H5F3O2/c1-3(9)2-4(10)5(6,7)8/h2H2,1H3Key: SHXHPUAKLCCLDV-UHFFFAOYSA-N
SMILES
  • CC(=O)CC(=O)C(F)(F)F
Properties
Chemical formula C5H4F3O2
Molar mass 153.080 g·mol
Appearance colorless liquid
Density 1.27 g/cm
Hazards
GHS labelling:
Pictograms GHS02: FlammableGHS07: Exclamation mark
Signal word Warning
Hazard statements H226, H302, H312, H315, H319, H332
Precautionary statements P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P312, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P370+P378, P403+P235, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
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. It is prepared by condensation of esters of trifluoroacetic acid with acetone.

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.

References

  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. 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. 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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