Dibenzylideneacetone

Dibenzylideneacetone

Names
IUPAC name (1E, 4E)-1,5-Diphenylpenta-1,4-dien-3-one
Other names Dibenzalacetone
Identifiers
CAS Number	538-58-9 undefined Y 35225-79-7 (E,E) N 115587-57-0 (E,Z) N 58321-78-1 (Z,Z) N
3D model (JSmol)	undefined: Interactive image (E,E): Interactive image (E,Z): Interactive image (Z,Z): Interactive image
ChemSpider	86113 undefined N 555548 (E,E) N 1266463 (E,Z) N 1266462 (Z,Z) N
ECHA InfoCard	100.007.908
PubChem CID	95417 undefined 640180 (E,E) 1549622 (E,Z) 1549621 (Z,Z)
UNII	9QXO7BCY9L (E,E) N N4SH2VDI6Y (E,Z) N 5L4OCE3E5U (Z,Z) N
InChI undefined: InChI=1S/C17H14O/c18-17(13-11-15-7-3-1-4-8-15)14-12-16-9-5-2-6-10-16/h1-14H Key: WMKGGPCROCCUDY-UHFFFAOYSA-N (E,E): InChI=1S/C17H14O/c18-17(13-11-15-7-3-1-4-8-15)14-12-16-9-5-2-6-10-16/h1-14H/b13-11+,14-12+ Key: WMKGGPCROCCUDY-PHEQNACWSA-N (E,Z): InChI=1S/C17H14O/c18-17(13-11-15-7-3-1-4-8-15)14-12-16-9-5-2-6-10-16/h1-14H/b13-11-,14-12+ Key: WMKGGPCROCCUDY-HEEUSZRZSA-N (Z,Z): InChI=1S/C17H14O/c18-17(13-11-15-7-3-1-4-8-15)14-12-16-9-5-2-6-10-16/h1-14H/b13-11-,14-12- Key: WMKGGPCROCCUDY-XSYHWHKQSA-N
SMILES undefined: O=C(C=C1ccccc1)C=Cc2ccccc2 (E,E): O=C(/C=C/c1ccccc1)/C=C/c2ccccc2 (E,Z): O=C(\C=C\c1ccccc1)/C=C\c2ccccc2 (Z,Z): O=C(/C=C\c1ccccc1)/C=C\c2ccccc2
Properties
Chemical formula	C17H14O
Molar mass	234.29 g/mol
Appearance	Yellow solid
Melting point	*Aldrich 110-111 °C (trans, trans isomer) Merck 60 °C (cis, trans isomer)
Boiling point	130 °C (266 °F; 403 K) (cis, cis isomer) *Merck
Solubility in water	insoluble
Hazards
Main hazards	Irritant
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Dibenzylideneacetone or dibenzalacetone, often abbreviated dba, is an organic compound with the formula C₁₇H₁₄O. It is a pale-yellow solid insoluble in water, but soluble in ethanol. Dibenzylideneacetone is used as a component in sunscreens and as a ligand in organometallic chemistry.

The compound can be prepared in the laboratory through condensation of benzaldehyde and acetone with sodium hydroxide in a water/ethanol medium with the exclusive formation of the trans, trans isomer (melting point 110–111 °C).

This reaction is frequently encountered in organic chemistry education as a laboratory procedure. The conversion proceeds via the intermediacy of benzylideneacetone.

Prolonged exposure to sunlight converts the compound in a [2+2] cycloaddition to a mixture of four cyclobutane isomers.

Dibenzylideneacetone is a component of the catalyst tris(dibenzylideneacetone)dipalladium(0). It is a labile ligand that is easily displaced by triphenylphosphine, hence it serves a useful entry point into palladium(0) chemistry.