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6-Bromo-3-hydroxypicolinic acid

  • CAS No. 321596-58-1

  • Cat. No. CS-0054192
  • Molecule weight218.00
  • Purity≥95%
  • MDL No.None

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

6-Bromo-3-hydroxypicolinic acid|CS-0054192

Structure of 321596-58-1

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General Information

  • CAS No. 321596-58-1
  • Cat. No. CS-0054192
  • Purity ≥95%
  • MDL No. None
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₄BrNO₃
  • Molecular Weight 218.00
  • Synonym(s) 6-BroMo-3-hydroxypyridine-2-carboxylic acid
  • SMILES O=C(O)C1=NC(Br)=CC=C1O

Description

6-Bromo-3-hydroxypicolinic acid features a bromine substituent at the 6-position and a hydroxyl group at the 3-position of the picolinic acid scaffold. This combination imparts enhanced reactivity for cross-coupling transformations while maintaining solubility in polar solvents. The molecule serves as a key building block for functionalized heterocycles in medicinal chemistry and materials science.

Application

6-Bromo-3-hydroxypicolinic acid serves as a versatile building block for the synthesis of bioactive heterocycles and pharmaceutical intermediates. The molecule combines a bromine handle at the 6-position with a reactive hydroxyl group at C3, enabling palladium-catalyzed cross-coupling and regioselective derivatization. Its stability under standard bench conditions and compatibility with common protecting group strategies facilitate efficient downstream functionalization in medicinal chemistry campaigns.

Synthesis

  • Route1

    References

    • INOVACIA AB Patent: WO2009/150144 A1, 2009 ; Location in patent: Page/Page column 63 ; WO 2009/150144 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

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Computational Chemistry Data

  • TPSA   70.42
  • LogP   1.2479
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   1

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