1,1,1-Trifluoroacetylacetone

Trifluoroacetylacetone.png skin-invert-image 1,1,1-Trifluoropentane-2,4-dione 1,1,1-Trifluoro-2,4-pentanedione, (trifluoroacetyl)acetone, 1,1,1-(trifluoroacetyl)acetone, 1,1,1-TFAA 367-57-7 66573 73943 206-698-5 9N20A8G8SW 1S/C5H5F3O2/c1-3(9)2-4(10)5(6,7)8/h2H2,1H3 SHXHPUAKLCCLDV-UHFFFAOYSA-N CC(=O)CC(=O)C(F)(F)F 5 4 3 2 colorless liquid 1.27 g/cm3 Warning 02 07 226 302 312 315 319 332 210 233 240 241 242 243 261 264 270 271 280 301+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 CF3C(O)CH2C(O)CH3. It is a colorless liquid. Like other 1,3-diketones, it is used as a precursor to heterocycles, e.g. pyrazoles, and metal chelates.M. L. Morris Ross W. Moshier Robert E. Sievers Inorganic Syntheses Tetrakis(1,1,1-trifluoro-2,4-pentanedionato)zirconium(and Hafnium) 1967 9 50–52 10.1002/9780470132401.ch15 9780470132401 It is prepared by condensation of esters of trifluoroacetic acid with acetone.Alkaline condensation of fluorinated esters with esters and ketones Henne, Albert L. Newman, Melvin S. Quill, Laurence L. Staniforth, Robert A. Journal of the American Chemical Society 1947 69 7 1819–20 10.1021/ja01199a075 1947JAChS..69.1819H 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.Keto-Enol Tautomerism in β-Dicarbonyls Studied by Nuclear Magnetic Resonance Spectroscopy. I. Proton Chemical Shifts and Equilibrium Constants of Pure Compounds Jane L. Burdett Max T. Rogers J. Am. Chem. Soc. 1964 86 11 2105–2109 10.1021/ja01065a003 1964JAChS..86.2105B References Category:Chelating agents Category:Diketones Category:Trifluoromethyl ketones Category:3-Hydroxypropenals