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 ;
3D model (JSmol)	Interactive image;
ChemSpider	21106446 ;
ECHA InfoCard	100.014.719
PubChem CID	24874462;
CompTox Dashboard (EPA)	DTXSID701336251 DTXSID4061753, DTXSID701336251 ;
	InChI InChI=1S/C5H2F6O2/c6-4(7,8)2(12)1-3(13)5(9,10)11/h1H2 Key: QAMFBRUWYYMMGJ-UHFFFAOYSA-N ; 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
	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 [77 °F], 100 kPa). verify (what is ?) 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

^ 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ 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.
^ 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:10.1016/S0022-328X(00)90307-3.

[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.{{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 (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:10.1016/S0022-328X(00)90307-3.

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