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2,4-Dioxo-2,4-dihydro-1H-benzo[d][1,3]oxazine-6-carboxylic acid

  • CAS No. 77423-13-3

  • Cat. No. CS-0149779
  • Purity≥95%
  • MDL No.MFCD08704695

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

2,4-Dioxo-2,4-dihydro-1H-benzo[d][1,3]oxazine-6-carboxylic acid|CS-0149779

Structure of 77423-13-3

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General Information

  • CAS No. 77423-13-3
  • Cat. No. CS-0149779
  • Purity ≥95%
  • MDL No. MFCD08704695
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₅NO₅
  • Molecular Weight 207.14
  • Synonym(s) 2,4-Dioxo-1,4-dihydro-2H-3,1-benzoxazine-6-carboxylic acid
  • SMILES O=C(O)C1=CC=2C(OC(NC2C=C1)=O)=O

Description

This oxazine carboxylic acid features a fused heterocyclic core with dual ketone and carboxylic acid functionalities, enabling direct integration into bioactive molecule scaffolds. The electron-deficient aromatic system supports efficient coupling reactions, while the bench-stable structure facilitates handling under standard conditions.

Application

Serves as a versatile building block for heterocyclic synthesis, particularly in the construction of bioactive benzoxazine scaffolds. The conjugated diketone and carboxylic acid functionalities enable sequential functionalization via condensation, cyclization, and derivatization reactions. Exhibits bench stability and facilitates straightforward purification, making it suitable for medicinal chemistry campaigns and process development workflows.

Synthesis

  • Route1
    • null|null
      32315-10-9
    • In-stock
      4-Aminoisophthalic acid|CS-0159419
      33890-03-8
    • ~%
    • In-stock
      2,4-Dioxo-2,4-dihydro-1H-benzo[d][1,3]oxazine-6-carboxylic acid|CS-0149779
      77423-13-3

    References

    • WO2012/59442 A2, ; Page/Page column 81-82 ; WO 2012/059442 A2
  • Route2

    References

    • Journal of Medicinal Chemistry, , vol. 24, # 6 p. 735 - 742
  • Route3
    • null|null
      89-87-2
    • ~%
    • In-stock
      2,4-Dioxo-2,4-dihydro-1H-benzo[d][1,3]oxazine-6-carboxylic acid|CS-0149779
      77423-13-3

    References

    • WO2012/59442 A2, ; WO 2012/059442 A2

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07,GHS09
Signal Word : Warning
UN#: 3077
Class : 9
Packing Group : Ⅲ
Hazard Statements : H315-H317-H319-H400
Precautionary Statements : P261-P264-P273-P280-P391

Quality Control

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Computational Chemistry Data

  • TPSA   100.37
  • LogP   0.1795
  • H_Acceptors   4
  • H_Donors   2
  • Rotatable_Bonds   1

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