Dibenzylideneacetone

Dibenzylideneacetone
  • CAS No.:538-58-9
Other grades of this product :
Dibenzylideneacetone Basic information
Product Name:Dibenzylideneacetone
Synonyms:DIBENZYLIDENEACETONE;DIBENZAL ACETONE;DISTYRYL KETONE;1,5-DIPHENYL-PENTA-1,4-DIEN-3-ONE;1,5-DIPHENYL-3-PENTADIENONE;1,5-DIPHENYL-1,4-PENTADIEN-3-ONE;1,5-Diphenyl-1,4-pentadien-3-one, min. 98%;AKOS 213-33
CAS:538-58-9
MF:C17H14O
MW:234.29
EINECS:208-697-5
Product Categories:Achiral Oxygen
Mol File:538-58-9.mol
Dibenzylideneacetone Chemical Properties
Melting point 107-113 °C
Boiling point 336.62°C (rough estimate)
density 1.0477 (rough estimate)
refractive index 1.5000 (estimate)
storage temp. Sealed in dry,Room Temperature
form solid
color yellow
Stability:Stable. Incompatible with strong oxidizing agents. Combustible.
InChIKeyWMKGGPCROCCUDY-UHFFFAOYSA-N
CAS DataBase Reference538-58-9(CAS DataBase Reference)
EPA Substance Registry System1,4-Pentadien-3-one, 1,5-diphenyl- (538-58-9)
Safety Information
Safety Statements 22-24/25
WGK Germany 3
HS Code 2914790090
MSDS Information
ProviderLanguage
SigmaAldrich English
ACROS English
ALFA English
Dibenzylideneacetone Usage And Synthesis
Chemical Propertiestrans,trans-Dibenzylideneacetone is a crystalline solid, melting point 110-111℃; cis-trans is a light yellow needle crystal, melting point 60℃; cis-cis is a yellow oily liquid, boiling point 130℃ (2.7Pa). Soluble in ethanol, acetone, chloroform, insoluble in water.
UsesDibenzylideneacetone is used as a ligand to prepare palladium catalysts, which are widely used in catalytic hydrogenation, coupling, carbonylation, alkyne ring trimerization, etc.
PreparationDibenzylideneacetone is obtained by the reaction of benzaldehyde and acetone. The reaction was carried out in aqueous ethanol solution at a reaction temperature of 20-25°C with a yield of 78%.
Synthesis Reference(s)Chemistry Letters, 9, p. 51, 1980The Journal of Organic Chemistry, 45, p. 3840, 1980 DOI: 10.1021/jo01307a022Organic Syntheses, Coll. Vol. 2, p. 167, 1943
Purification MethodsCrystallise the ketone from hot ethyl acetate (2.5mL/g) or EtOH. [Beilstein 7 IV 1747.]
Dibenzylideneacetone Preparation Products And Raw materials

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