1,1,1-Trifluoroacetylacetone

1,1,1-Trifluoroacetylacetone
Names
	Preferred IUPAC name 1,1,1-Trifluoropentane-2,4-dione
	Other names 1,1,1-Trifluoro-2,4-pentanedione, (trifluoroacetyl)acetone, 1,1,1-(trifluoroacetyl)acetone, 1,1,1-TFAA
Identifiers
CAS Number	367-57-7;
3D model (JSmol)	Interactive image;
ChemSpider	66573;
ECHA InfoCard	100.006.090
EC Number	206-698-5;
PubChem CID	73943;
UNII	9N20A8G8SW;
CompTox Dashboard (EPA)	DTXSID3059896 ;
	InChI InChI=1S/C5H5F3O2/c1-3(9)2-4(10)5(6,7)8/h2H2,1H3 Key: SHXHPUAKLCCLDV-UHFFFAOYSA-N;
	SMILES CC(=O)CC(=O)C(F)(F)F;
Properties
Chemical formula	C5H4F3O2
Molar mass	153.080 g·mol−1
Appearance	colorless liquid
Density	1.27 g/cm3
Hazards
GHS pictograms
GHS Signal word	Warning
GHS hazard statements	H226, H302, H312, H315, H319, H332
GHS precautionary statements	P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+312, P302+352, P303+361+353, P304+312, P304+340, P305+351+338, P312, P321, P322, P330, P332+313, P337+313, P362, P363
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

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.[1] It is prepared by condensation of esters of trifluoroacetic acid with acetone.[2]

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.[3]

References

Morris, M. L.; Moshier, Ross W.; Sievers, Robert E. (1967). Tetrakis(1,1,1-trifluoro-2,4-pentanedionato)zirconium (and Hafnium). Inorg. Synth. Inorganic Syntheses. 9. pp. 50–52. doi:10.1002/9780470132401.ch15. ISBN 9780470132401.
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.
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.

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[Sievers-1] Morris, M. L.; Moshier, Ross W.; Sievers, Robert E. (1967). Tetrakis(1,1,1-trifluoro-2,4-pentanedionato)zirconium (and Hafnium). Inorg. Synth. Inorganic Syntheses. 9. pp. 50–52. doi:10.1002/9780470132401.ch15. ISBN 9780470132401.

[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] 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.