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Methyl 6-bromo-5-hydroxy-2-pyridinecarboxylate

  • CAS No. 170235-19-5

  • Cat. No. CS-B1159
  • Molecule weight232.03
  • Purity≥98%
  • MDL No.MFCD09878491

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

Methyl 6-bromo-5-hydroxy-2-pyridinecarboxylate|CS-B1159

Structure of 170235-19-5

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General Information

  • CAS No. 170235-19-5
  • Cat. No. CS-B1159
  • Purity ≥98%
  • MDL No. MFCD09878491
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₆BrNO₃
  • Molecular Weight 232.03
  • Synonym(s) 6-bromo-5-hydroxy-pyridine-2-carboxylic acid methyl ester
  • SMILES OC1=CC=C(C(OC)=O)N=C1Br

Description

Methyl 6-bromo-5-hydroxy-2-pyridinecarboxylate features a brominated pyridine core with orthogonal functional groups enabling direct coupling in cross-coupling reactions. The hydroxyl moiety offers a site for derivatization, while the ester group facilitates selective transformations. This bench-stable compound integrates readily into complex heterocyclic scaffolds under standard conditions.

Application

Methyl 6-bromo-5-hydroxy-2-pyridinecarboxylate serves as a versatile building block in heterocyclic synthesis, enabling direct functionalization at the C5 hydroxyl and C6 bromide positions. The molecule exhibits bench stability and compatibility with palladium-catalyzed cross-coupling reactions, facilitating access to substituted pyridine scaffolds. Its dual reactive handles—electrophilic bromide and nucleophilically modifiable hydroxyl—support sequential transformations for medicinal chemistry applications.

Synthesis

  • Route1

    References

    • Kelly, T. Ross; Lang, Fengrui Journal of Organic Chemistry, 1996 , vol. 61, # 14 p. 4623 - 4633
  • Route2
    • null|null
      186581-53-3
    • 6-Bromo-5-hydroxypicolinic acid|CS-0328486
      178876-92-1
    • ~42%
    • In-stock
      Methyl 6-bromo-5-hydroxy-2-pyridinecarboxylate|CS-B1159
      170235-19-5
    • In-stock
      Methyl 6-bromo-5-methoxypicolinate|CS-0041484
      170235-18-4

    References

    • Kelly, T. Ross; Lang, Fengrui Journal of Organic Chemistry, 1996 , vol. 61, # 14 p. 4623 - 4633
  • Route3

    References

    • LUMIPHORE, INC.; MAGDA, Darren; XU, Jide; BUTLIN, Nathaniel, G. Patent: WO2014/78690 A1, 2014 ;

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   59.42
  • LogP   1.3363
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   1

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