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CS-W001157 4
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5-Hydroxypicolinaldehyde

  • CAS No. 31191-08-9

  • Cat. No. CS-W005647
  • Molecule weightNone
  • Purity≥95%
  • MDL No.MFCD10697538

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

5-Hydroxypicolinaldehyde|CS-W005647

Structure of 31191-08-9

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General Information

  • CAS No. 31191-08-9
  • Cat. No. CS-W005647
  • Purity ≥95%
  • MDL No. MFCD10697538
  • Storage -20°C, sealed storage, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₅NO₂
  • Molecular Weight None
  • Synonym(s) 5-hydroxypyridine-2-carbaldehyde
  • SMILES O=CC1=NC=C(O)C=C1

Description

5-Hydroxypicolinaldehyde features a pyridine ring with strategically positioned aldehyde and hydroxyl groups, enabling versatile coordination in transition metal complexes. The ortho-hydroxyl facilitates chelation, while the aldehyde group supports nucleophilic additions. This bifunctional scaffold integrates readily into ligand design for catalysis and molecular recognition applications under standard conditions.

Application

5-Hydroxypicolinaldehyde serves as a versatile building block in synthetic organic chemistry, enabling efficient access to bioactive heterocycles and metal-chelating scaffolds. Its ortho-hydroxy aldehyde functionality facilitates intramolecular cyclization and coordination with transition metals, while the pyridine ring supports further functionalization via electrophilic substitution or cross-coupling reactions. The compound exhibits sufficient bench stability for routine handling and is compatible with common purification methods, making it well-suited for medicinal chemistry campaigns and catalyst development.

Synthesis

  • Route1

    References

    • Seredyuk; Gaspar; Ksenofontov; Galyametdinov; Kusz; Guetlich Journal of the American Chemical Society, 2008 , vol. 130, # 4 p. 1431 - 1439
  • Route2
    • null|null
      31191-11-4
    • ~65%
    • In-stock
      5-Hydroxypicolinaldehyde|CS-W005647
      31191-08-9

    References

    • Hass, Werner; Koenig, Wilfried A. Liebigs Annalen der Chemie, 1982 , # 9 p. 1615 - 1622
  • Route3
    • 6-(Acetoxymethyl)pyridin-3-yl acetate|CS-0662304
      31181-78-9
    • ~%
    • In-stock
      5-Hydroxypicolinaldehyde|CS-W005647
      31191-08-9

    References

    • Liebigs Annalen der Chemie, , # 9 p. 1615 - 1622

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   50.19
  • LogP   0.5997
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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