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;
	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
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 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.

This organofluorine compound was first prepared by the condensation of ethyl ester of trifluoroacetic acid and 1,1,1-trifluoroacetone.^[2] It has been investigated as an etchant for copper and its complexes, such as Cu(Hfac)(trimethylvinylsilane) have been employed as precursors in microelectronics.^[3]

Being highly electrophilic, hexafluoroacetylacetone is hydrated in water to give the tetraol.^[4]

References

↑ 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.
↑ 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.
↑ 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:10.1002/cber.19891220218.

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[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] 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.

[3] 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.

[4] 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.