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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==
<references/> <references/>


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Latest revision as of 22:12, 3 March 2024

"HFAC" redirects here. For House Foreign Affairs Committee, see United States House Committee on Foreign Affairs. For the arts building at Brigham Young University, see Harris Fine Arts Center. For the animal agriculture labeling organization, see Humane Farm Animal Care.
Hexafluoroacetylacetone
Names
IUPAC name 1,1,1,5,5,5-hexafluoro-pentane-2,4-dione
Other names Hexafluoroacetylacetone, HfacH
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.014.719 Edit this at Wikidata
PubChem CID
UNII
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 to 71 °C (158 to 160 °F; 343 to 344 K)
Solubility in water organic solvents
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 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.

Metal complexes of the conjugate base exhibit enhanced volatility and Lewis acidity relative to analogous complexes derived from acetylacetone. The visible spectra of bis(hexafluoroacetylacetonato)copper(II) and its dehydrate have been reported in carbon tetrachloride. Compounds of the type bis(hexafluoroacetylacetonato)copper(II):Bn , 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.

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.

Being highly electrophilic, hexafluoroacetylacetone is hydrated in water to give the tetraol.

References

  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. Bertrand, J. A..; Kaplan, R. I. (1965). "A Study of Bis(hexafluoroacetylacetonató)copper(II)". Inorganic Chemistry. 5 (3): 489–491. doi:10.1021/ic50037a039.
  3. Partenheimer, W.; Drago, R. S. (1970). "Preparation and Thermodynamic Data for Adducts of Bases with Some Copper(II) 0-Diketonates". Inorganic Chemistry. 9: 47–52. doi:10.1021/ic50083a009.
  4. Cramer, R. E.; Bopp, T. T. (1977). "Graphical display of the enthalpies of adduct formation for Lewis acids and bases". Journal of Chemical Education. 54: 612–613. doi:10.1021/ed054p612.
  5. 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.
  6. 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.
  7. 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 (2): 315. doi:10.1002/cber.19891220218.
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