Benzalacetone (1896-62-4, 122-57-6)

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Suppliers

• Sigma-Aldrich - Benzalacetone
  34.50 - 812.00 USD
• Fisher Scientific - Search for Benzalacetone
• TCI - Benzalacetone
  14.00 - 52.00 USD

Most-cited Publications

• Identification of an antibacterial compound, benzylideneacetone, from Xenorhabdus nematophila against major plantpathogenic bacteria (Fems Microbiology Letters, 2004)
• Benzalacetone synthase. A novel polyketide synthase that plays a crucial role in the biosynthesis of phenylbutanones in Rheum palmatum. (FEBS Journal, 2001)
• On the way to chiral copper(I) arenethiolate catalysts for the enantioselective conjugate addition of methyl lithium and methyl magnesium iodide to benzylideneacetone (Tetrahedron-asymmetry, 1991)
• Preparation, Characterization, and Performance of the Supported Hydrogen-Bonded Ruthenium Catalyst [(sulphos)Ru(NCMe)3](OSO2CF3)/SiO2. Comparisons with Analogous Homogeneous and Aqueous-Biphase Catalytic Systems in the Hydrogenation of Benzylideneacetone and Benzonitrile (Organometallics, 2000)
• Modification of chemical reactivity upon cyclodextrin encapsulation: : Asymmetric bromination of chalcone and benzylideneacetone (Tetrahedron, 1994)
• Site-directed Mutagenesis of Benzalacetone Synthase THE ROLE OF PHE215 IN PLANT TYPE III POLYKETIDE SYNTHASES (Journal of Biological Chemistry, 2003)

Areas of Application

Safety

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Trends

Alternate Names

• benzylideneacetone
• t-PBO
• benzylideneacetone, (E)-isomer
• trans-4-phenyl-3-buten-2-one
• 4-phenylbutenone
• 4-phenyl-3-buten-2-one
• benzylideneacetone, (Z)-isomer
• SMILES
  CC(=O)C=CC1=CC=CC=C1
• InChIKey
  BWHOZHOGCMHOBV-UHFFFAOYSA-N

External Links

• Pubchem - Benzalacetone
• Wikipedia - trans-benzylideneacetone
  Benzylideneacetone is the organic compound described by the formula C6H5CH=CHC(O)CH3. Although both cis- and trans-isomers are possible for the ,-unsaturated ketone, only the trans isomer is observed. Its original preparation demonstrated the scope of condensation reactions to construct new, complex organic compounds.

Synthesis

methylglyoxal  +  BENZYL CHLORIDE (Wittig)

Acetonitrile  +  Chlorostyrene (Grignard carbonyl)

STYRENE  +  ACETYL CHLORIDE (Heck terminal vinyl)

3-Buten-2-ol, 4-phenyl-, (3Z)-  +  dimethyl sulfide (Corey-Kim oxidation of secondary alcohols)

CID 12492652  +  1-Hydroxy-1,2-benziodoxol-3(1H)-one 1-oxide (Nicolaou IBX dehydrogenation)

Reactant  +  CHLOROBENZENE (Stille)

Synthesis of Benzalacetone ›

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Benzalacetone

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