Dibenzoylmethane

Dibenzoylmethane

Names
IUPAC name 1,3-diphenylpropane-1,3-dione
Other names 2-Benzoylacetophenone
Identifiers
CAS Number	120-46-7
ChemSpider	8126
Jmol interactive 3D	Image
PubChem	8433
InChI InChI=1S/C15H12O2/c16-14(12-7-3-1-4-8-12)11-15(17)13-9-5-2-6-10-13/h1-10H,11H2 Key: NZZIMKJIVMHWJC-UHFFFAOYSA-N InChI=1/C15H12O2/c16-14(12-7-3-1-4-8-12)11-15(17)13-9-5-2-6-10-13/h1-10H,11H2 Key: NZZIMKJIVMHWJC-UHFFFAOYAS
SMILES C1=CC=C(C=C1)C(=O)CC(=O)C2=CC=CC=C2
Properties
Chemical formula	C15H12O2
Molar mass	224.25 g/mol
Melting point	77 to 78 °C (171 to 172 °F; 350 to 351 K)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

1,3-Diphenyl-1,3-propanedione (dibenzoylmethane, DBM) is an aromatic 1,3-diketone derivative of acetylacetone (acac), where both methyl groups in acac have been substituted by phenyl groups. It is a white solid melting at 77−78 °C. Similar to acac, DBM exists in two tautomeric forms, with the keto-enol equilibrium of DBM shifting strongly towards the enol form, particularly in non-polar solvents such as benzene.^[1] This is the result of the stability of the intramolecular hydrogen bond in the cis-enol form which is further resonance-stabilized by conjugation with phenyl rings. Due to its high photostability, derivatives of DBM such as avobenzone, have found applications as sunscreen products.

References

1. , Jan Zawadiak, Marek Mrzyczek; Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 75 (2010) pp. 925-929