Benzoylacetone

Benzoylacetone
Names
	IUPAC name 1-phenylbutane-1,3-dione
Identifiers
CAS Number	93-91-4;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL3186793;
ChemSpider	6898;
ECHA InfoCard	100.002.080
EC Number	202-286-4;
PubChem CID	7166;
UNII	I3RUV8U115;
CompTox Dashboard (EPA)	DTXSID3021803 ;
	InChI InChI=1S/C10H10O2/c1-8(11)7-10(12)9-5-3-2-4-6-9/h2-6H,7H2,1H3 Key: CVBUKMMMRLOKQR-UHFFFAOYSA-N;
	SMILES CC(=O)CC(=O)C1=CC=CC=C1;
Properties
Chemical formula	C10H10O2
Molar mass	162.188 g·mol−1
Density	1.0599 g/cm3
Melting point	56 °C (133 °F; 329 K)
Boiling point	261.5 °C (502.7 °F; 534.6 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P271, P280, P302 P352, P304 P340, P305 P351 P338, P312, P321, P332 P313, P337 P313, P362, P403 P233, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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 (pK_a=8.7) forms stable complexes with transition metals and lanthanides.^[3]

References

^ 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.
^ 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.
^ 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.

[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] 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] 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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