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CS-W001157 4
Total: USD 88.00

4-Hydroxypyridine-2-carboxylic acid

  • CAS No. 22468-26-4

  • Cat. No. CS-W002643
  • Purity≥95%
  • MDL No.None

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

4-Hydroxypyridine-2-carboxylic acid|CS-W002643

Structure of 22468-26-4

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General Information

  • CAS No. 22468-26-4
  • Cat. No. CS-W002643
  • Purity ≥95%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₅NO₃
  • Molecular Weight 139.11
  • Synonym(s) 4-Hydroxypicolinic acid
  • SMILES O=C(C1=NC=CC(O)=C1)O

Description

4-Hydroxypyridine-2-carboxylic acid features a dual functional group architecture combining a phenolic hydroxyl and a carboxylic acid at ortho positions on a pyridine ring. This arrangement enables strong intramolecular hydrogen bonding, enhancing stability and influencing coordination behavior in metal complexes. The molecule serves as a versatile scaffold for ligand design in catalysis and pharmaceutical development.

Application

4-Hydroxypyridine-2-carboxylic acid serves as a versatile building block in medicinal chemistry, enabling the synthesis of bioactive heterocycles through established coupling and cyclization protocols. Its dual functionality—phenolic hydroxyl and carboxylic acid—facilitates orthogonal derivatization, enhances solubility, and supports metal chelation in transition-metal-catalyzed transformations. The compound exhibits good bench stability and is readily purified by recrystallization or column chromatography, making it suitable for scalable synthesis workflows.

Synthesis

  • Route1

    References

    • Journal fuer Praktische Chemie (Leipzig), , vol. <2> 148, p. 13,16
  • Route2

    References

    • Journal of Medicinal Chemistry, , vol. 34, # 1 p. 90 - 97
  • Route3

    References

    • Pharmaceutical Bulletin, , vol. 2, p. 137

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   70.42
  • LogP   0.4854
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   1

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