Hexafluoroacetylacetone

Hexafluoroacetylacetone

Names
IUPAC name 1,1,1,5,5,5-Hexafluoro-2,4-pentanedione
Other names Hexafluoroacetylacetone, HfacH
Identifiers
CAS Number	1522-22-1 Y
3D model (Jmol)	Interactive image
ChemSpider	21106446 Y
ECHA InfoCard	100.014.719
PubChem	24874462
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
Hazards
Main hazards	toxic
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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.^[1] It has been investigated as an etchant for copper and its complexes, such as Cu(Hfac)(trimethylvinylsilane) have been employed as precursors in microelectronics.^[2]

Being highly electrophilic, hfac hydrates in water to give the tetraol.^[3]

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 (7): 1819–20. doi:10.1021/ja01199a075. 
2. ↑ 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. 
3. ↑ 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: 315. doi:10.1002/cber.19891220218.