Dibenzylidene acetone

Structural formula
	(1 E , 4 E ) -1,5-diphenylpenta-1,4-dien-3-one ; ( trans , trans isomer)
General
Surname	Dibenzylidene acetone
other names	(1 U , 4 U ) -1,5-diphenyl-1,4-pentadien-3-one ( IUPAC ) ; Dibenzalacetone;
Molecular formula	C 17 H 14 O
External identifiers / databases
EC number	609-096-4
ECHA InfoCard	100.126.050
PubChem	640180
ChemSpider	555548
Wikidata	Q417585
properties
Molar mass	234.29 g mol −1
Physical state	firmly
density	1.11 g cm −3 (25 ° C)
Melting point	trans - trans 112-114 ° C ; cis - trans 60 ° C ;
boiling point	cis - cis 130 ° C ;
solubility	almost insoluble in water
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Dibenzylidene acetone or dibenzalacetone (abbreviation: dba) is an organic chemical compound and is one of the ketones . It is used in organometallic chemistry , for example as a ligand on palladium . The most common form is the trans - trans form, but the isomeric cis - cis and cis - trans forms also occur.

Dibenzylidene acetone powder

presentation

Dibenzylideneacetone is synthesized by aldol condensation of acetone with two equivalents of benzaldehyde . If a ratio of one equivalent of acetone and 2.2 equivalents of benzaldehyde is chosen, i.e. an excess of benzaldehyde, yields of 90 to 94% are obtained.

Individual evidence

^ Carl L. Yaws: Thermophysical Properties of Chemicals and Hydrocarbons. William Andrew Verlag, Norwich 2008, ISBN 978-0-8155-1596-8 , p. 277.
↑ ^a ^b ^c ^d data sheet dibenzylidene acetone from AlfaAesar, accessed on December 4, 2013 ( PDF )(JavaScript required) .
↑ ^a ^b J. G. Dinwiddie HM White, WJ Day: The Geometrical Isomers of 1,5-Diphenylpentadiene-3-one ; J. Org. Chem. 1962, 27, 1, 327-328 (1962) doi : 10.1021 / jo01048a529
↑ ^a ^b data sheet dibenzylidene acetone from Sigma-Aldrich , accessed on December 4, 2013 ( PDF ).
↑ Patent DE102007018703 : Palladium (0) -dibenzylidene acetone complexes. Registered on April 18, 2007 , published on October 23, 2008 , applicant: WC Heraeus , inventors: Horst Meyer, Steffen Voss, Richard Walter. ‌
↑ G. Venkateshwarlu, B. Subrahmanyam: Conformations of dibenzylideneacetone: An IR spectroscopic study . Proc. Indian Acad. Sci. - Chem. Sci., Vol. 99, Nos. 5-6, pp. 419-424, December 1987.
^ Charles R. Conard, Morris A. Dolliver: Dibenzalacetone In: Organic Syntheses . 12, 1932, p. 22, doi : 10.15227 / orgsyn.012.0022 ; Coll. Vol. 2, 1943, pp. 167-168 ( PDF ).

Web links

Commons : Dibenzylidene Acetone - Collection of Images, Videos, and Audio Files

[1] Carl L. Yaws: Thermophysical Properties of Chemicals and Hydrocarbons. William Andrew Verlag, Norwich 2008, ISBN 978-0-8155-1596-8 , p. 277.

[alfa-2] ta sheet dibenzylidene acetone from AlfaAesar, accessed on December 4, 2013 ( PDF )(JavaScript required) .

[dinwiddie-3] J. G. Dinwiddie HM White, WJ Day: The Geometrical Isomers of 1,5-Diphenylpentadiene-3-one ; J. Org. Chem. 1962, 27, 1, 327-328 (1962) doi : 10.1021 / jo01048a529

[ALDRICH-4] ta sheet dibenzylidene acetone from Sigma-Aldrich , accessed on December 4, 2013 ( PDF ).

[5] Patent DE102007018703 : Palladium (0) -dibenzylidene acetone complexes. Registered on April 18, 2007 , published on October 23, 2008 , applicant: WC Heraeus , inventors: Horst Meyer, Steffen Voss, Richard Walter. ‌

[6] G. Venkateshwarlu, B. Subrahmanyam: Conformations of dibenzylideneacetone: An IR spectroscopic study . Proc. Indian Acad. Sci. - Chem. Sci., Vol. 99, Nos. 5-6, pp. 419-424, December 1987.

[7] Charles R. Conard, Morris A. Dolliver: Dibenzalacetone In: Organic Syntheses . 12, 1932, p. 22, doi : 10.15227 / orgsyn.012.0022 ; Coll. Vol. 2, 1943, pp. 167-168 ( PDF ).