Hexafluoroacetylacetone
Names
IUPAC name
1,1,1,5,5,5-hexafluoro-pentane-2,4-dione
Other names
Hexafluoroacetylacetone, HfacH
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.014.719 Edit this at Wikidata
UNII
  • InChI=1S/C5H2F6O2/c6-4(7,8)2(12)1-3(13)5(9,10)11/h1H2 checkY
    Key: QAMFBRUWYYMMGJ-UHFFFAOYSA-N checkY
  • InChI=1/C5H2F6O2/c6-4(7,8)2(12)1-3(13)5(9,10)11/h1H2
    Key: QAMFBRUWYYMMGJ-UHFFFAOYAR
  • FC(F)(F)C(=O)CC(=O)C(F)(F)F
Properties
C5H2F6O2
Molar mass 208.06 g/mol
Appearance colourless liquid
Density 1.47 g/mL
Boiling point 70 to 71 °C (158 to 160 °F; 343 to 344 K)
organic solvents
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Hexafluoroacetylacetone is the chemical compound with the nominal formula CF3C(O)CH2C(O)CF3 (often abbreviated as hfacH). This colourless liquid is a ligand precursor and a reagent used in MOCVD. The compound exists exclusively as the enol CF3C(OH)=CHC(O)CF3. For comparison under the same conditions, acetylacetone is 85% enol.[1]

Metal complexes of the conjugate base exhibit enhanced volatility and Lewis acidity relative to analogous complexes derived from acetylacetone. The visible spectra of bis(hexafluoroacetylacetonato)copper(II) and its dehydrate have been reported in carbon tetrachloride.[2] Compounds of the type bis(hexafluoroacetylacetonato)copper(II):Bn , where :B are Lewis bases such as N,N-dimethylacetamide, dimethyl sulfoxide, or pyridine and n = 1 or 2, have been prepared. Since bis(hexafluoroacetylacetonato)copper(II) is soluble in carbon tetrachloride, its Lewis acid properties have been studied for 1:1 adducts using a variety of Lewis bases.[3][4]

This organofluorine compound was first prepared by the condensation of ethyl ester of trifluoroacetic acid and 1,1,1-trifluoroacetone.[5] It has been investigated as an etchant for copper and its complexes, such as Cu(Hfac)(trimethylvinylsilane) have been employed as precursors in microelectronics.[6]

Being highly electrophilic, hexafluoroacetylacetone is hydrated in water to give the tetraol.[7]

References

  1. ^ 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.
  2. ^ Bertrand, J. A..; Kaplan, R. I. (1965). "A Study of Bis(hexafluoroacetylacetonató)copper(II)". Inorganic Chemistry. 5 (3): 489–491. doi:10.1021/ic50037a039.
  3. ^ Partenheimer, W.; Drago, R. S. (1970). "Preparation and Thermodynamic Data for Adducts of Bases with Some Copper(II) 0-Diketonates". Inorganic Chemistry. 9: 47–52. doi:10.1021/ic50083a009.
  4. ^ Cramer, R. E.; Bopp, T. T. (1977). "Graphical display of the enthalpies of adduct formation for Lewis acids and bases". Journal of Chemical Education. 54: 612–613. doi:10.1021/ed054p612.
  5. ^ 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.
  6. ^ Mark J. Hampden-Smith; Toivo T. Kodas (1995). "Chemical vapour deposition of copper from (hfac)CuL compounds". Polyhedron. 14 (6): 699–732. doi:10.1016/0277-5387(94)00401-Y.
  7. ^ Aygen, S.; van Eldik, R. (1989). "A Spectroscopic and Mechanistic Study of the Enolization and Diol Formation of Hexafluoroacetylacetone in the Presence of Water and Alcohol". Chem. Ber. 122 (2): 315. doi:10.1002/cber.19891220218.
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