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2-Oxo-2,3-dihydro-1,3-benzoxazole-6-carboxylic acid

  • CAS No. 54903-16-1

  • Cat. No. CS-0006553
  • Purity≥97%
  • MDL No.MFCD11179328

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

2-Oxo-2,3-dihydro-1,3-benzoxazole-6-carboxylic acid|CS-0006553

Structure of 54903-16-1

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General Information

  • CAS No. 54903-16-1
  • Cat. No. CS-0006553
  • Purity ≥97%
  • MDL No. MFCD11179328
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₅NO₄
  • Molecular Weight 179.13
  • Synonym(s) benzoxazolin-2-one-6-carboxylic acid
  • SMILES O=C(C1=CC=C2NC(OC2=C1)=O)O

Description

2-Oxo-2,3-dihydro-1,3-benzoxazole-6-carboxylic acid features a fused heterocyclic core with a carboxylic acid at the 6-position, enabling direct conjugation in synthetic workflows. The oxazole ring imparts stability and electron-deficient character, facilitating coupling reactions under mild conditions. This scaffold integrates readily into bioactive molecule design, particularly for kinase inhibitors and pharmaceutical intermediates.

Application

2-Oxo-2,3-dihydro-1,3-benzoxazole-6-carboxylic acid serves as a versatile building block in medicinal chemistry, enabling the synthesis of bioactive heterocycles through standard amide coupling and electrophilic substitution reactions. Its carboxylic acid functionality facilitates direct derivatization, while the fused benzoxazole core provides metabolic stability and enhanced binding affinity in target-directed scaffolds. The compound exhibits good bench stability and is readily purified by recrystallization, supporting its use in scalable route development.

Synthesis

  • Route1

    References

    • RESVERLOGIX CORP.; JOHANSSON, Jan, O.; HANSEN, Henrik, C.; CHIACCHIA, Fabrizio, S.; WONG, Norman, C.W. Patent: WO2007/16525 A2, 2007 ; Location in patent: Page/Page column 89 ; WO 2007/016525 A2
  • Route2
    • null|null
      207552-92-9
    • ~79%
    • In-stock
      2-Oxo-2,3-dihydro-1,3-benzoxazole-6-carboxylic acid|CS-0006553
      54903-16-1

    References

    • AMGEN INC. Patent: WO2009/11871 A2, 2009 ; Location in patent: Page/Page column 203 ; WO 2009/011871 A2
  • Route3
    • null|null
      861312-43-8
    • ~%
    • In-stock
      2-Oxo-2,3-dihydro-1,3-benzoxazole-6-carboxylic acid|CS-0006553
      54903-16-1

    References

    • Journal of the Chemical Society, , vol. 119, p. 1431

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

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Computational Chemistry Data

  • TPSA   83.3
  • LogP   0.8193
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   1

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