110–111 °C (230–232 °F; 383–384 K) (trans, trans isomer)[2]
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).
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Infobox references
Chemical compound
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.
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).[3][4][5]
^ abMerck index
^Cite error: The named reference OrgSynth was invoked but never defined (see the help page).
^Claisen, L.; Claparède, A. (1881). "Ueber Verbindungen des Acetons und Mesityloxds mit Benzaldehyd und über die Constitution des Acetophorons" [On compounds of acetone and mesityl oxide with benzaldehyde and on the composition of phorone]. Berichte der Deutschen Chemischen Gesellschaft (in German). 14: 349–353. doi:10.1002/cber.18810140182. ; see pp. 350–351.
^Claisen wrote that the German chemist Adolf Baeyer might have synthesized dibenzylideneacetone as early as 1866, although the evidence wasn't clear.
(Claisen & Claparède, 1881), p. 350: "Die Einwirkung wasserentziehender Mittel auf ein solches Gemenge ist schon von Baeyer1) flüchtig untersucht worden. Nach ihm entsteht als Endprodukt ein gelbes, in Alkohol unlösliches Harz, als Zwischenprodukt ein ölförmiger, unzersetzt siedender und cumarinartig riechender Körper, der, wie er meint, das Methylketon der Zimmtsäure darstellt." (The effect of a dehydrating agent on such a mixture has already been briefly investigated by Baeyer1). According to him, a yellow resin [that's] insoluble in alcohol arises as a final product, [and] as an intermediate, [there arises] an oily substance [which] boils without decomposing and smells like coumarin [and] which, he thinks, represents the methyl ketone of cinnamic acid.)
Baeyer, Adolf (1866). "Ueber Condensation und Polymerie" [On condensation and polymerism]. Annalen der Chemie und Pharmacie (in German). 5 (Supplement): 79–95. ; see p. 82. From p. 82: "Um für diese Ansicht noch einen weiteren Beweis beizubringen, habe ich ein Gemenge von Bittermandelöl und Aceton mit wasserentziehenden Mitteln, Salzsäure, Schwefelsäure, Kali behandelt. Die Condensation erfolgt ausserordentlich schnell, schon nach wenigen Minuten, und nach einiger Zeit verharzt die ganze Masse. Das Endproduct ist ein gelbes Harz, das in Aether löslich und durch Alkohol daraus als gelbes Pulver gefällt wird, welches schwach nach Rhabarber riecht. Die Analyse gab keine verständlichen Zahlen, daher ist die Substanz wahrscheinlich ein Gemenge. Zuerst bildet sich aber ein öliger, unzersetzt flüchtiger Körper, der einen an Cumarin erinnernden Geruch besitzt, und der höchst wahrscheinlich das Methylaceton der Zimmtsäure ist: … ." (In order to provide further proof for this view, I have treated a mixture of benzaldehyde and acetone with dehydrating agents [e.g.,] hydrochloric acid, sulfuric acid, potash. The condensation occurs extraordinarily quickly, after just a few minutes, and after some time the whole mass becomes resinous. The final product is a yellow resin, which [is] soluble in ether and is precipitated therefrom by alcohol as a yellow powder, which smells faintly of rhubarb. Analysis [to determine its empirical formula] produced no intelligible numbers, so the substance is probably a mixture. Initially, however, an oily, stable, volatile substance is formed, which has a smell recalling coumarin, and which is very likely the methyl acetone of cinnamic acid: … .)
^For biographical information about Charles-Claude-Alexandre Claparède (with photograph), see: Reverdin, Frédéric (1914) "Dr. Alexandre Claparède. 1858–1913," Verhandlungen der Schweizerischen Naturforschenden Gesellschaft: Nekrologe und Biographien verstorbener Mitglieder … (Proceedings of the Swiss Society of Natural Sciences: Obituaries and biographies of deceased members … ), 96 : 22–27. (in French)
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Dibenzylideneacetone or dibenzalacetone, often abbreviated dba, is an organic compound with the formula C17H14O. It is a pale-yellow solid insoluble in...
Claisen-Schmidt condensation with another molecule of benzaldehyde to form dibenzylideneacetone. Because relatively weak bases such as NaOH make very little of the...
tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3), is prepared by reducing sodium tetrachloropalladate in the presence of dibenzylideneacetone. Palladium(0)...
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tetrachloropalladate, to which dibenzylideneacetone (dba) and acetylacetonate may be coordinated to form tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3)...
Negishi coupling of hexaiodidobenzene and diferrocenylzinc, using tris(dibenzylideneacetone)dipalladium(0) as catalyst, in tetrahydrofuran: The yield is only...
the type PhCHX2 and PhCH= substituents (Ph = C6H5). For example, dibenzylideneacetone is (PhCH=CH)2CO. Benzal chloride, PhCHCl2, is alternatively named...
Fe(C5H5)2, molybdenum hexacarbonyl Mo(CO)6, triethylborane Et3B, Tris(dibenzylideneacetone)dipalladium(0) Pd2(dba)3) Clusters can be found in all classes of...
hexaferrocenylbenzene: with hexaiodidobenzene, diferrocenylzinc and tris(dibenzylideneacetone)dipalladium(0) in tetrahydrofuran. The yield is only 4% signifying...
The first reported asymmetric rearrangement is catalyzed by tris(dibenzylideneacetone)dipalladium(0) and the Trost ligand: A similar reaction uses additional...
conjugate addition: The catalyst system in this reaction is tris(dibenzylideneacetone)dipalladium(0) / tricyclohexylphosphine. Another conjugate addition...
metals as found in (benzylideneacetone)iron tricarbonyl and tris(dibenzylideneacetone)dipalladium(0). Metal alkene complexes. Bis(cyclooctadiene)nickel(0)...
and a salt such as ammonium chloride . The catalyst system is tris(dibenzylideneacetone)dipalladium(0) with triphenylarsine: A common alteration to the Stille...
partners were a tosylhydrazone, an aryl halide with catalyst system dibenzylideneacetone / XPhos. As part of the catalytic cycle the diazo intermediateformed...
there are many types, attached to a normal flask. Cinnamic acid Dibenzylideneacetone Tetrahedral carbonyl addition compound Lassar-Cohn (1906). Arbeitsmethoden...
sequence are a Suzuki-Miyaura coupling with an ionic liquid and Tris(dibenzylideneacetone)dipalladium(0) and a Heck reaction with another palladium catalyst...
nanoparticles can also be synthesized by decomposing Pt2(dba)3 (dba = dibenzylideneacetone) under a CO or H2 atmosphere, in the presence of a capping agent...
iodide 1 in a Stille reaction in presence of carbon monoxide (tris(dibenzylideneacetone)dipalladium(0), triphenylarsine). The internal double in 3 was converted...
substrates with catalytic [Pd2(dba)3]CHCl3 and triphenylphosphine (dba =dibenzylideneacetone) (Scheme 13). Mycophenolic acid is a Penicillium metabolite that...