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
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.126.050
PubChem CID
UNII
  • 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
C17H14O
Molar mass 234.29 g/mol
Appearance Yellow solid
Melting point
  • 110–111 °C (230–232 °F; 383–384 K) (trans, trans isomer)
  • 60 °C (140 °F; 333 K) (cis, trans isomer)
Boiling point 130 °C (266 °F; 403 K) (cis, cis isomer)
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).
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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).

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