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{{Redirect|HFAC|House Foreign Affairs Committee|United States House Committee on Foreign Affairs|the arts building at Brigham Young University|Harris Fine Arts Center|the animal agriculture labeling organization|Humane Farm Animal Care}}
{{Orphan|date=February 2009}}
{{chembox {{chembox
|Watchedfields = changed
| verifiedrevid = 400832793 |verifiedrevid = 455252402
| ImageFile = Hfac.png |ImageFile = Hfacenol.png
| ImageSize =
| IUPACName = 1,1,1,5,5,5-Hexafluoro-2,4-pentanedione |IUPACName = 1,1,1,5,5,5-hexafluoro-pentane-2,4-dione
| OtherNames = Hexafluoroacetylacetone, HfacH |OtherNames = Hexafluoroacetylacetone, HfacH
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| InChI = 1/C5H2F6O2/c6-4(7,8)2(12)1-3(13)5(9,10)11/h1H2 |InChI = 1/C5H2F6O2/c6-4(7,8)2(12)1-3(13)5(9,10)11/h1H2
| InChIKey = QAMFBRUWYYMMGJ-UHFFFAOYAR |InChIKey = QAMFBRUWYYMMGJ-UHFFFAOYAR
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C5H2F6O2/c6-4(7,8)2(12)1-3(13)5(9,10)11/h1H2 |StdInChI = 1S/C5H2F6O2/c6-4(7,8)2(12)1-3(13)5(9,10)11/h1H2
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = QAMFBRUWYYMMGJ-UHFFFAOYSA-N |StdInChIKey = QAMFBRUWYYMMGJ-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}} |CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 1522-22-1 |CASNo = 1522-22-1
|UNII_Ref = {{fdacite|correct|FDA}}
⚫ | PubChem = 24874462
|UNII = MG8477QRV4
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ |PubChem = 73706
| ChemSpiderID=21106446
⚫ |ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ | SMILES = FC(F)(F)C(=O)CC(=O)C(F)(F)F
|ChemSpiderID =21106446
⚫ |SMILES = FC(F)(F)C(=O)CC(=O)C(F)(F)F
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| Formula = C<sub>5</sub>H<sub>2</sub>F<sub>6</sub>O<sub>2</sub> |Formula = C<sub>5</sub>H<sub>2</sub>F<sub>6</sub>O<sub>2</sub>
| MolarMass = 208.06 g/mol |MolarMass = 208.06 g/mol
| Appearance = colourless liquid |Appearance = colourless liquid
| Density = 1.47 g/mL |Density = 1.47 g/mL
|BoilingPtC = 70 to 71
| MeltingPt =
⚫ |Solubility = organic solvents
| BoilingPt = 70-71 °C
⚫ | Solubility = organic solvents
⚫ }}
| Section3 = {{Chembox Hazards
| MainHazards = toxic
| FlashPt =
| Autoignition =
}}
}} }}
⚫ }}

'''Hexafluoroacetylacetone''' is the ] with the nominal ] CF<sub>3</sub>C(O)CH<sub>2</sub>C(O)CF<sub>3</sub> (often abbreviated as hfacH). This colourless liquid is a ] precursor and a reagent used in ]. The compound exists exclusively as the ] CF<sub>3</sub>C(OH)=CHC(O)CF<sub>3</sub>. For comparison under the same conditions, ] is 85% enol.<ref>{{cite journal|title=Keto-Enol Tautomerism in β-Dicarbonyls Studied by Nuclear Magnetic Resonance Spectroscopy. I. Proton Chemical Shifts and Equilibrium Constants of Pure Compounds|author1=Jane L. Burdett|author2=Max T. Rogers|journal=J. Am. Chem. Soc.|year=1964|volume=86|pages=2105–2109|doi=10.1021/ja01065a003}}</ref>

]es of the conjugate base exhibit enhanced volatility and ]ity relative to analogous complexes derived from ].
The visible spectra of bis(hexafluoroacetylacetonato)copper(II) and its dehydrate have been reported in carbon tetrachloride.<ref>{{cite journal|author1=Bertrand, J. A.. |author2=Kaplan, R. I. |year=1965|title= A Study of Bis(hexafluoroacetylacetonató)copper(II)|journal=Inorganic Chemistry|volume=5|issue=3|pages=489–491|doi=10.1021/ic50037a039}}</ref>
Compounds of the type bis(hexafluoroacetylacetonato)copper(II):B<sub>n</sub> , 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.<ref>{{cite journal|author1=Partenheimer, W. |author2=Drago, R. S. |year=1970|title= Preparation and Thermodynamic Data for Adducts of Bases with Some Copper(II) 0-Diketonates|journal=Inorganic Chemistry|volume=9|pages=47–52|doi=10.1021/ic50083a009}}</ref><ref>{{cite journal|author1=Cramer, R. E. |author2=Bopp, T. T. |year=1977|title= Graphical display of the enthalpies of adduct formation for Lewis acids and bases |journal= Journal of Chemical Education |volume=54|pages=612–613|doi= 10.1021/ed054p612}}</ref>


⚫ This ] compound was first prepared by the ] of ] ] of ] and ].<ref>{{cite journal |author1=Henne, Albert L. |author2=Newman, Melvin S. |author3=Quill, Laurence L. |author4=Staniforth, Robert A. | title = Alkaline condensation of fluorinated esters with esters and ketones | year = 1947 | journal = ] | volume = 69 | issue = 7| pages = 1819–20 | doi =10.1021/ja01199a075 }}</ref> It has been investigated as an etchant for copper and its complexes, such as Cu(Hfac)(trimethylvinylsilane) have been employed as precursors in ].<ref>{{cite journal |author1=Mark J. Hampden-Smith |author2=Toivo T. Kodas | title = Chemical vapour deposition of copper from (hfac)CuL compounds | year = 1995 | journal = ] | volume = 14 | issue = 6| pages = 699–732 | doi = 10.1016/0277-5387(94)00401-Y}}</ref>
'''Hexafluoroacetylacetone''' is the ] with the ] CF<sub>3</sub>C(O)CH<sub>2</sub>C(O)CF<sub>3</sub> (often abbreviated as hfac). This colourless liquid is a ] precursor and a reagent used in ]. Complexes of the conjugate base, often called Hfac<sup>-</sup>, exhibit enhanced volatility and ]ity relative to analogous complexes derived from ].


Being highly electrophilic, hexafluoroacetylacetone is hydrated in water to give the tetraol.<ref>{{cite journal|last2=van Eldik|first2=R.|year=1989|title=A Spectroscopic and Mechanistic Study of the Enolization and Diol Formation of Hexafluoroacetylacetone in the Presence of Water and Alcohol|journal=Chem. Ber.|volume=122|issue=2|page=315|doi=10.1002/cber.19891220218|last1=Aygen|first1=S.}}</ref>
⚫ This ] compound was first prepared by the ] of ] ] of ] and 1,1,1-trifluoroacetone.<ref>{{cite journal | author = Henne, Albert L.; Newman, Melvin S.; Quill, Laurence L.; Staniforth, Robert A. | title = Alkaline condensation of fluorinated esters with esters and ketones | year = 1947 | journal = ] | volume = 69 | issue = | pages = 1819–20 | doi =10.1021/ja01199a075 }}</ref> It has been investigated as an etchant for copper and its complexes, such as Cu(Hfac)(trimethylvinylsilane) have been employed as precursors in ].<ref>{{cite journal | author = Mark J. Hampden-Smith, Toivo T. Kodas | title = Chemical vapour deposition of copper from (hfac)CuL compounds | year = 1995 | journal = ] | volume = 14 | issue = | pages = 699–732 | doi = 10.1016/0277-5387(94)00401-Y}}</ref>


==References== ==References==
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