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CS-W001157 4
Total: USD 88.00

Dibenzylideneacetone

  • CAS No. 538-58-9

  • Cat. No. CS-M0452
  • Purity≥98%
  • MDL No.MFCD00004790

*For research and further manufacturing use only, not for direct human use.

Dibenzylideneacetone|CS-M0452

Structure of 538-58-9

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General Information

  • CAS No. 538-58-9
  • Cat. No. CS-M0452
  • Purity ≥98%
  • MDL No. MFCD00004790
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₇H₁₄O
  • Molecular Weight 234.30
  • Synonym(s) Dibenzalacetone
  • SMILES O=C(/C=C/C1=CC=CC=C1)/C=C/C2=CC=CC=C2

Description

Dibenzylideneacetone serves as a versatile ligand in transition metal catalysis, featuring a conjugated enone system that enables robust coordination to palladium and nickel centers. This stable, bench-ready compound integrates efficiently into cross-coupling and cyclization reactions, delivering predictable reactivity under standard conditions.

Application

Dibenzylideneacetone serves as a versatile building block in transition-metal-catalyzed cross-coupling reactions, particularly as a stable ligand precursor in palladium and nickel catalysis. Its conjugated enone system facilitates coordination to metal centers, enhancing catalyst stability and reactivity in Suzuki-Miyaura, Stille, and Negishi couplings. The compound exhibits excellent bench stability, ease of handling, and compatibility with diverse functional groups, making it a practical choice for synthetic workflows requiring robust ligand systems in pharmaceutical and materials chemistry applications.

Synthesis

  • Route1
    • null|null
      100-52-7
    • null|null
      67-64-1
    • ~94%
    • In-stock
      Dibenzylideneacetone|CS-M0452
      538-58-9

    References

    • Journal of Chemical Research, , # 1 p. 55 - 56
  • Route2
    • null|null
      100-52-7
    • Benzylideneacetone Warfarin Impurity|CS-0229511
      122-57-6
    • ~91%
    • In-stock
      Dibenzylideneacetone|CS-M0452
      538-58-9

    References

    • Synthetic Communications, , vol. 40, # 19 p. 2887 - 2896
  • Route3
    • null|null
      100-52-7
    • null|null
      67-64-1
    • ~%
    • In-stock
      Dibenzylideneacetone|CS-M0452
      538-58-9
    • Benzylideneacetone Warfarin Impurity|CS-0229511
      122-57-6

    References

    • Annales de Chimie (Cachan, France), , vol. <10>9, p. 17

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   17.07
  • LogP   3.9823
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   4

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