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CS-W001157 4
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3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carboxylic acid

  • CAS No. 134997-87-8

  • Cat. No. CS-0067802
  • Purity≥98%
  • MDL No.MFCD03036647

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

3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carboxylic acid|CS-0067802

Structure of 134997-87-8

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General Information

  • CAS No. 134997-87-8
  • Cat. No. CS-0067802
  • Purity ≥98%
  • MDL No. MFCD03036647
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₇NO₄
  • Molecular Weight 193.16
  • Synonym(s) 3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylic acid
  • SMILES O=C(C1=CC=C(OCC(N2)=O)C2=C1)O

Description

This oxazine carboxylic acid features a fused heterocyclic core with orthogonal functional groups enabling direct integration into medicinal chemistry scaffolds. The electron-deficient ring system supports selective derivatization, while the carboxylic acid moiety provides a handle for conjugation under standard coupling conditions.

Application

3-Oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carboxylic acid serves as a versatile heterocyclic building block for medicinal chemistry campaigns, enabling access to bioactive scaffolds via standard functionalization protocols. Its fused oxazine core exhibits bench stability and tolerates diverse reaction conditions, facilitating coupling, derivatization, and cyclization steps in multistep synthesis. The carboxylic acid group provides a handle for amide formation and conjugation, while the ketone functionality supports nucleophilic addition and condensation reactions. This compound functions effectively in both solution-phase and solid-phase synthetic workflows.

Synthesis

  • Route1
    • null|null
      598-21-0
    • In-stock
      3-Amino-4-hydroxybenzoic acid|CS-W010940
      1571-72-8
    • ~92%
    • In-stock
      3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carboxylic acid|CS-0067802
      134997-87-8

    References

    • Goodman, Krista B.; Neeb, Michael J.; Sehon, Clark A.; Viet, Andrew Q.; Wang, Gren Z. Patent: US2008/21023 A1, 2008 ; Location in patent: Page/Page column 122-123 ; US 20080021023 A1
  • Route2

    References

    • Justus Liebigs Annalen der Chemie, , vol. 311, p. 168
  • Route3
    • null|null
      79-04-9
    • In-stock
      3-Amino-4-hydroxybenzoic acid|CS-W010940
      1571-72-8
    • ~73%
    • In-stock
      3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carboxylic acid|CS-0067802
      134997-87-8

    References

    • TAKEDA CHEMICAL INDUSTRIES, LTD. Patent: WO2004/46107 A1, 2004 ; Location in patent: Page 209-210 ; WO 2004/046107 A1

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   75.63
  • LogP   0.7157
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   1

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