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.

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[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.