Dibenzoylmethane
 | |
| Names | |
|---|---|
| IUPAC name
1,3-diphenylpropane-1,3-dione | |
| Other names
2-Benzoylacetophenone | |
| Identifiers | |
120-46-7  | |
| ChemSpider | 8126  |
| |
| Jmol-3D images | Image |
| PubChem | 8433 |
| |
| Properties | |
| C15H12O2 | |
| Molar mass | 224.25 g/mol |
| Melting point | 77 to 78 °C (171 to 172 °F; 350 to 351 K)[1] |
| Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | |
| verify (what is: /?) | |
| 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.