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 ; 35225-79-7 (E,E) ; 115587-57-0 (E,Z) ; 58321-78-1 (Z,Z) ;
3D model (JSmol)	undefined: Interactive image; (E,E): Interactive image; (E,Z): Interactive image; (Z,Z): Interactive image;
ChEMBL	ChEMBL17201 (E,E) ;
ChemSpider	86113 undefined ; 555548 (E,E) ; 1266463 (E,Z) ; 1266462 (Z,Z) ;
ECHA InfoCard	100.126.050
PubChem CID	95417 undefined; 640180 (E,E); 1549622 (E,Z); 1549621 (Z,Z);
UNII	9QXO7BCY9L (E,E) ; N4SH2VDI6Y (E,Z) ; 5L4OCE3E5U (Z,Z) ;
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=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
	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). verify (what is ?) 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.

Preparation

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).^[1]

Dibenzalacetone synthesis

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

Reactions and derivatives

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

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.

References

^ Conard, C. R.; Dolliver, M. A. (1943). "Dibenzalacetone". Organic Syntheses{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 2, p. 167.
^ Rao, G. N.; Janardhana, C.; Ramanathan, V.; Rajesh, T.; Kumar, P. H. (November 2006). "Photochemical Dimerization of Dibenzylideneacetone. A Convenient Exercise in [2+2] Cycloaddition Using Chemical Ionization Mass Spectrometry". J. Chem. Educ. 83 (11): 1667. doi:10.1021/ed083p1667.

[1] Conard, C. R.; Dolliver, M. A. (1943). "Dibenzalacetone". Organic Syntheses{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 2, p. 167.

[2] Rao, G. N.; Janardhana, C.; Ramanathan, V.; Rajesh, T.; Kumar, P. H. (November 2006). "Photochemical Dimerization of Dibenzylideneacetone. A Convenient Exercise in [2+2] Cycloaddition Using Chemical Ionization Mass Spectrometry". J. Chem. Educ. 83 (11): 1667. doi:10.1021/ed083p1667.

[1]

[2]