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 labelling:
Pictograms
Signal word	Warning
Hazard statements	H226, H302, H312, H315, H319, H332
Precautionary statements	P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P312, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P370+P378, P403+P235, P501
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

1. Morris, M. L.; Moshier, Ross W.; Sievers, Robert E. (1967). "Tetrakis(1,1,1-trifluoro-2,4-pentanedionato)zirconium(and Hafnium)". Inorganic Syntheses. Vol. 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. Bibcode:1947JAChS..69.1819H. 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 (11): 2105–2109. Bibcode:1964JAChS..86.2105B. doi:10.1021/ja01065a003.