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CS-W001157 4
Total: USD 88.00

3-Benzoylacrylic acid

  • CAS No. 583-06-2

  • Cat. No. CS-0040775
  • Purity≥96%
  • MDL No.MFCD00014015

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

3-Benzoylacrylic acid|CS-0040775

Structure of 583-06-2

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General Information

  • CAS No. 583-06-2
  • Cat. No. CS-0040775
  • Purity ≥96%
  • MDL No. MFCD00014015
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₈O₃
  • Molecular Weight 176.17
  • Synonym(s) 4-oxo-4-phenylbut-2-enoic acid
  • SMILES O=C(O)/C=C/C(C1=CC=CC=C1)=O

Description

3-Benzoylacrylic acid features a conjugated system linking a benzoyl group to an α,β-unsaturated carboxylic acid moiety. This structure enables participation in Michael additions and Diels-Alder reactions, serving as a key building block in synthetic organic chemistry. The compound exhibits stability under standard bench conditions and facilitates efficient access to complex heterocyclic frameworks through controlled reactivity at the double bond.

Application

3-Benzoylacrylic acid serves as a versatile building block for synthesizing substituted cinnamic acid derivatives and functionalized heterocycles. Its α,β-unsaturated carboxylic acid structure enables reliable Michael additions, Diels–Alder cycloadditions, and palladium-catalyzed coupling reactions. The molecule exhibits good bench stability and facilitates straightforward purification via recrystallization, making it well-suited for scalable synthesis in medicinal chemistry and materials development.

Synthesis

  • Route1
    • null|null
      108-31-6
    • null|null
      71-43-2
    • ~58%
    • In-stock
      3-Benzoylacrylic acid|CS-0040775
      583-06-2

    References

    • Pant, Umesh C.; Gaur, B. S.; Chugh, Manju Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1987 , vol. 26, # 1-12 p. 947 - 950
  • Route2
    • 2-Hydroxy-4-oxo-4-phenylbutanoic acid|CS-0669349
      65245-10-5
    • ~%
    • In-stock
      3-Benzoylacrylic acid|CS-0040775
      583-06-2

    References

    • Chemische Berichte, , vol. 26, p. 555
  • Route3
    • null|null
      33093-73-1
    • ~%
    • In-stock
      3-Benzoylacrylic acid|CS-0040775
      583-06-2

    References

    • Bulletin de la Societe Chimique de France, , p. 2598 - 2606

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS06
Signal Word : Danger
UN#: 2811
Class : 6.1
Packing Group : Ⅱ
Hazard Statements : H301-H315-H319-H335
Precautionary Statements : P264-P270-P330-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   54.37
  • LogP   1.5101
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   3

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