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43143 Aldrich

trans,trans-Dibenzylideneacetone

≥98.0% (HPLC)

Synonym: 1,5-Diphenyl-1,4-pentadien-3-one, trans,trans-1,5-Diphenyl-1,4-pentadien-3-one

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Properties

Related Categories Building Blocks, C15 to C38, Carbonyl Compounds, Chemical Synthesis, Ketones,
InChI Key   WMKGGPCROCCUDY-PHEQNACWSA-N
assay   ≥98.0% (HPLC)
mp   104-107 °C(lit.)
  107-113 °C
solubility   dichloromethane: soluble25 mg/mL, clear

Description

Application

Reactant involved in:
• Nazarov-like cyclization
• Transfer hydrogenation
• Lewis acid mediated condensation
• Hetero-Diels-Alder reactions
• Asymmetric 1,4-addition reactions
• Michael addition reactions

General description

trans,trans-Dibenzylideneacetone (dba) participates as an additive in the copper-catalyzed N-arylation of imidazoles. dba acts as ligand. It has an important influence on the reactivity of palladium(0) complexes generated in situ from the mixtures of Pd(dba)2 and phosphine ligands. Photolysis of trans,trans-dibenzylideneacetone (1,5-diphenylpenta-1,4-dien-3-one) in benzene solution affords the truxinic-type dimer. It is a reactive dienone and readily forms carbo- or heterocyclic compounds with many nucleophiles. Dibenzylideneacetone forms a stable zero-valent, neutral complex with palladium(0), Pd(dba)2. It also participates in the preparation of Pd2(dba)3(solvent) complexes. These palladium(0)-dibenzylideneacetone complexes are important catalysts.

Price and Availability

Suggested Laboratory Gloves


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Safety & Documentation

Safety Information

WGK Germany 
3
Protocols & Articles
Peer-Reviewed Papers
15

References

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