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Bicyclo[4.2.0]octa-1,3,5-triene-3-carboxylic acid

  • CAS No. 875-94-5

  • Cat. No. CS-0155370
  • Molecule weight148.16
  • Purity≥97%
  • MDL No.MFCD09842339

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

Bicyclo[4.2.0]octa-1,3,5-triene-3-carboxylic acid|CS-0155370

Structure of 875-94-5

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General Information

  • CAS No. 875-94-5
  • Cat. No. CS-0155370
  • Purity ≥97%
  • MDL No. MFCD09842339
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₈O₂
  • Molecular Weight 148.16
  • Synonym(s) Cyclobutabenzene-4-carboxylicacid
  • SMILES C1CC2=CC(=CC=C12)C(=O)O

Description

Bicyclo[4.2.0]octa-1,3,5-triene-3-carboxylic acid features a rigid, electron-deficient tricyclic framework with a conjugated diene system and a carboxylic acid handle at the bridgehead position. This structure enables direct participation in Diels-Alder cycloadditions and serves as a strategic scaffold for synthesizing complex polycyclic architectures under mild conditions.

Application

Bicyclo[4.2.0]octa-1,3,5-triene-3-carboxylic acid serves as a versatile synthetic building block for strained bicyclic systems, enabling efficient access to functionalized carbocyclic scaffolds via Diels-Alder cycloadditions and subsequent transformations. The conjugated triene-carboxylic acid motif provides robust reactivity in electrophilic functionalization and offers excellent stability under standard bench conditions, facilitating straightforward purification and integration into complex molecular architectures relevant to natural product synthesis and medicinal chemistry.

Synthesis

  • Route1

    References

    • Tetrahedron, , vol. 20, p. 2185 - 2194
  • Route2
    • null|null
      19369-50-7
    • ~%
    • In-stock
      Bicyclo[4.2.0]octa-1,3,5-triene-3-carboxylic acid|CS-0155370
      875-94-5

    References

    • Justus Liebigs Annalen der Chemie, , vol. 714, p. 91 - 111
  • Route3
    • 1-(Bicyclo[4.2.0]octa-1(6),2,4-trien-3-yl)ethan-1-one|CS-0674304
      875-93-4
    • ~%
    • In-stock
      Bicyclo[4.2.0]octa-1,3,5-triene-3-carboxylic acid|CS-0155370
      875-94-5

    References

    • Tetrahedron, , vol. 20, p. 2185 - 2194

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-P330-P362+P364-P405-P501

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Computational Chemistry Data

  • TPSA   37.3
  • LogP   1.4834
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   1

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