Dibenzoylmethane

Dibenzoylmethane
IUPAC name 1,3-diphenylpropane-1,3-dione
Other names 2-Benzoylacetophenone
Identifiers
CAS number	120-46-7 Y
PubChem	8433
Jmol-3D images	Image 1
SMILES C1=CC=C(C=C1)C(=O)CC(=O)C2=CC=CC=C2
Properties
Molecular formula	C15H12O2
Molar mass	224.25 g/mol
Melting point	77-78°C [1]
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

1,3-diphenylpropane-1,3-dione (dibenzoylmethane, DBM) is an aromatic 1,3-diketone, acetylacetone (acac) derivative, where both methyl groups have been substituted by phenyl groups. It is white solid melting 77-78°C. Similiary to acac, DBM exist as two tautomeric forms, however keto-enol equilibrium of DBM is strongly shifted to the enol form. It is result of formation of intra-molecular hydrogen bond, which is conjugated with phenyl rings ^[1]. The resonance-assisted hydrogen bond is responsible for high photostability of such compounds, and therefore, some derivates of DBM (e.g. Avobenzone) have found application as sunscreens.

References

1. ^ ^{a b} [1], Jan Zawadiak, Marek Mrzyczek; Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 75 (2010) pp. 925-929