Dibenzylideneacetone

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

Names
Preferred IUPAC name (1E,4E)-1,5-Diphenylpenta-1,4-dien-3-one
Other names Dibenzalacetone
Identifiers
CAS Number	538-58-9 non-specific Y 35225-79-7 (E,E) Y 115587-57-0 (E,Z) Y 58321-78-1 (Z,Z) Y
3D model (JSmol)	undefined: Interactive image (E,E): Interactive image (E,Z): Interactive image (Z,Z): Interactive image
ChEMBL	ChEMBL17201 (E,E) N
ChemSpider	86113 undefined N 555548 (E,E) N 1266463 (E,Z) N 1266462 (Z,Z) N
ECHA InfoCard	100.126.050
PubChem CID	95417 undefined 640180 (E,E) 1549622 (E,Z) 1549621 (Z,Z)
UNII	9QXO7BCY9L (E,E) Y N4SH2VDI6Y (E,Z) Y 5L4OCE3E5U (Z,Z) Y
CompTox Dashboard (EPA)	DTXSID401274418
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=Cc1ccccc1)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	111 °C (232 °F; 384 K) (trans, trans isomer)[1] 60 °C (140 °F; 333 K) (cis, trans isomer)[1]
Boiling point	130 °C (266 °F; 403 K) (cis, cis isomer)[1]
Solubility in water	Insoluble
Solubility in other solvents	Soluble in acetone and chloroform, slightly soluble in ethanol.
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Irritant
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

It was first prepared in 1881 by the German chemist Rainer Ludwig Claisen (1851–1930) and the Swiss chemist Charles-Claude-Alexandre Claparède (14 April 1858 – 1 November 1913).^[2][3][4]

Preparation

Main article: Claisen-Schmidt condensation

The trans,trans isomer can be prepared in high yield and purity by condensation of benzaldehyde and acetone with sodium hydroxide in a water/ethanol medium followed by recrystallization.^[5]

This reaction, which proceeds via the intermediacy of benzylideneacetone, is often performed in organic chemistry classes,^[6] and is called Claisen-Schmidt condensation.

Reactions and derivatives

Prolonged exposure to sunlight initiates [2+2] cycloadditions, converting it to a mixture of dimeric and trimeric cyclobutane cycloadducts.^[7]

Uses

Dibenzylideneacetone is used as a component in sunscreens and as a ligand in organometallic chemistry.

For example, it 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.