1,1,1-Trifluoroacetylacetone

{{Chembox

|ImageFile = Trifluoroacetylacetone.png

|ImageClass = skin-invert-image

|PIN = 1,1,1-Trifluoropentane-2,4-dione

|OtherNames = 1,1,1-Trifluoro-2,4-pentanedione, (trifluoroacetyl)acetone, 1,1,1-(trifluoroacetyl)acetone, 1,1,1-TFAA

|Section1={{Chembox Identifiers

|CASNo = 367-57-7

|ChemSpiderID = 66573

|PubChem = 73943

|EC_number = 206-698-5

|UNII = 9N20A8G8SW

|InChI=1S/C5H5F3O2/c1-3(9)2-4(10)5(6,7)8/h2H2,1H3

|InChIKey = SHXHPUAKLCCLDV-UHFFFAOYSA-N

|SMILES = CC(=O)CC(=O)C(F)(F)F }}

|Section2={{Chembox Properties

|C=5|H=4|F=3|O=2

|Appearance = colorless liquid

|Density = 1.27 g/cm{{sup|3}}

}}

|Section3={{Chembox Hazards

|GHSSignalWord = Warning

|GHSPictograms = {{GHS02}}{{GHS07}}

|HPhrases = {{H-phrases|226|302|312|315|319|332}}

|PPhrases = {{P-phrases|210|233|240|241|242|243|261|264|270|271|280|301+312|302+352|303+361+353|304+312|304+340|305+351+338|312|321|322|330|332+313|337+313|362|363|370+378|403+235|501}}

}}

}}

1,1,1-Trifluoroacetylacetone is the organofluorine compound with the formula CF{{sub|3}}C(O)CH{{sub|2}}C(O)CH{{sub|3}}. It is a colorless liquid. Like other 1,3-diketones, it is used as a precursor to heterocycles, e.g. pyrazoles, and metal chelates.{{cite book|first1=M. L. |last1= Morris |first2=Ross W. |last2= Moshier |first3=Robert E.|last3= Sievers |title= Inorganic Syntheses |chapter= Tetrakis(1,1,1-trifluoro-2,4-pentanedionato)zirconium(and Hafnium) |date= 1967 |volume=9 |pages=50–52 |doi=10.1002/9780470132401.ch15|isbn= 9780470132401}} It is prepared by condensation of esters of trifluoroacetic acid with acetone.{{cite journal|title=Alkaline condensation of fluorinated esters with esters and ketones|author=Henne, Albert L.|author2=Newman, Melvin S.|author3=Quill, Laurence L.|author4=Staniforth, Robert A.|journal=Journal of the American Chemical Society |year=1947|volume=69|issue=7|pages=1819–20|doi=10.1021/ja01199a075}}

According to an analysis by proton NMR spectroscopy, the compound exists predominantly (97% at 33 °C, neat) as the enol. For comparison under the same conditions, the percent enol for acetylacetone and hexafluoroacetylacetone are 85 and 100%, respectively.{{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}}