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Hexafluoroacetylacetone

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Hexafluoroacetylacetone
Names
IUPAC name 1,1,1,5,5,5-Hexafluoro-2,4-pentanedione
Other names Hexafluoroacetylacetone, HfacH
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.014.719 Edit this at Wikidata
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C5H2F6O2/c6-4(7,8)2(12)1-3(13)5(9,10)11/h1H2Key: QAMFBRUWYYMMGJ-UHFFFAOYSA-N
  • InChI=1/C5H2F6O2/c6-4(7,8)2(12)1-3(13)5(9,10)11/h1H2Key: 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 70-71 °C
Solubility in water organic solvents
Hazards
Occupational safety and health (OHS/OSH):
Main hazards toxic
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Hexafluoroacetylacetone is the chemical compound with the formula CF3C(O)CH2C(O)CF3 (often abbreviated as hfac). This colourless liquid is a ligand precursor and a reagent used in MOCVD. Complexes of the conjugate base, often called Hfac, exhibit enhanced volatility and Lewis acidity relative to analogous complexes derived from acetylacetone.

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

References

  1. 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: 1819–20. doi:10.1021/ja01199a075.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  2. Mark J. Hampden-Smith, Toivo T. Kodas (1995). "Chemical vapour deposition of copper from (hfac)CuL compounds". Polyhedron. 14: 699–732. doi:10.1016/0277-5387(94)00401-Y.
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