Benzoylacetone

Benzoylacetone

Benzoylacetone

Chemical compound

Benzoylacetone is the organic compound with the nominal formula C6H5C(O)CH2C(O)CH3. As a 1,3-dicarbonyl, it is a precursor to many heterocycles, such as pyrazoles.[1] It exists predominantly as the enol tautomer C6H5C(OH)=CHC(O)CH3.[2] Its conjugate base (pKa=8.7) forms stable complexes with transition metals and lanthanides.[3]

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References

  1. [1]
    Penning, Thomas D.; Talley, John J.; Bertenshaw, Stephen R.; Carter, Jeffery S.; Collins, Paul W.; Docter, Stephen; Graneto, Matthew J.; Lee, Len F.; Malecha, James W.; Miyashiro, Julie M.; Rogers, Roland S.; Rogier, D. J.; Yu, Stella S.; Anderson, Gary D.; Burton, Earl G.; Cogburn, J. Nita; Gregory, Susan A.; Koboldt, Carol M.; Perkins, William E.; Seibert, Karen; Veenhuizen, Amy W.; Zhang, Yan Y.; Isakson, Peter C. (1997). "Synthesis and Biological Evaluation of the 1,5-Diarylpyrazole Class of Cyclooxygenase-2 Inhibitors: Identification of 4-[5-(4-Methylphenyl)-3- (Trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide (SC-58635, Celecoxib)". Journal of Medicinal Chemistry. 40 (9): 1347–1365. doi:10.1021/JM960803Q. PMID 9135032.
  2. [2]
    Jones, R. D. G. (1976). "The crystal and molecular structure of the enol form of 1-phenyl-1,3-butanedione (Benzoylacetone) by neutron diffraction". Acta Crystallographica Section B: Structural Crystallography and Crystal Chemistry. 32 (7): 2133–2136. doi:10.1107/S0567740876007267.
  3. [3]
    McGehee, M. D.; Bergstedt, T.; Zhang, C.; Saab, A. P.; o'Regan, M. B.; Bazan, G. C.; Srdanov, V. I.; Heeger, A. J. (1999). "Narrow Bandwidth Luminescence from Blends with Energy Transfer from Semiconducting Conjugated Polymers to Europium Complexes". Advanced Materials. 11 (16): 1349–1354. doi:10.1002/(SICI)1521-4095(199911)11:16<1349::AID-ADMA1349>3.0.CO;2-W.
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