Dibenzylideneacetone

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Dibenzylideneacetone
General
Systematic name	1,5-diphenylpenta-1,4-dien-3-one
Other names	bis(2-phenylethenyl)ketone, dibenzalacetone, styrol ketone, bis(2-phenylvinyl)ketone, dibenzylidineacetone, distyryl ketone
Molecular formula	C17H14O
SMILES	O=C(/C=C/c1ccccc1)/C=C/c2ccccc2
Molar mass	234.29 g/mol
Appearance	yellow solid
CAS number	[538-58-9]
Properties
Density and phase	? g/cm³, ?
Solubility in water	not soluble
Melting point	110 - 112°C (383 - 385 K) (trans-trans isomer only)
Related compounds	Methyl vinyl ketone
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Dibenzylideneacetone or dibenzalacetone or 1,5-diphenylpenta-1,4-dien-3-one is an organic compound.

The compound can be prepared in the laboratory by an aldol condensation of benzaldehyde and acetone with sodium hydroxide in a water / ethanol medium with the exclusive formation of the trans, trans isomer (melting point 107-111 °C).

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

Dibenzylideneacetone is used as a sunscreen component and it is used as a ligand in organometallic chemistry for instance in tris(dibenzylideneacetone)dipalladium(0)) or (dba)₃Pd₂.

Prolonged exposure to sunlight converts the compound in a [2+2]cycloaddition to a mixture of four cyclobutane isomers.^[1].

[edit] External links

• Dibenzalacetone Organic Syntheses, Coll. Vol. 2, p.167 (1943); Vol. 12, p.22 (1932) Article
• Lab procedure I
• Lab procedure II
• Datasheet commercial supplier
• Links to external chemical sources.

[edit] References