Hexafluoroacetylacetone

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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]

Hexafluoroacetylacetone

Names
IUPAC name 1,1,1,5,5,5-hexafluoro-pentane-2,4-dione
Other names Hexafluoroacetylacetone, HfacH
Identifiers
CAS Number	1522-22-1 Y
3D model (JSmol)	Interactive image
ChemSpider	21106446 Y
ECHA InfoCard	100.014.719
PubChem CID	73706
UNII	MG8477QRV4 Y
CompTox Dashboard (EPA)	DTXSID701336251 DTXSID4061753, DTXSID701336251
InChI InChI=1S/C5H2F6O2/c6-4(7,8)2(12)1-3(13)5(9,10)11/h1H2 Y Key: QAMFBRUWYYMMGJ-UHFFFAOYSA-N Y InChI=1/C5H2F6O2/c6-4(7,8)2(12)1-3(13)5(9,10)11/h1H2 Key: QAMFBRUWYYMMGJ-UHFFFAOYAR
SMILES FC(F)(F)C(=O)CC(=O)C(F)(F)F
Properties
Chemical formula	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)
Solubility in water	organic solvents
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

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):B_n , 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.