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CS-W001157 4
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5-Bromo-2-chloropyridin-3-ol

  • CAS No. 286946-77-8

  • Cat. No. CS-W003542
  • Purity≥96%
  • MDL No.MFCD08688592

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

5-Bromo-2-chloropyridin-3-ol|CS-W003542

Structure of 286946-77-8

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General Information

  • CAS No. 286946-77-8
  • Cat. No. CS-W003542
  • Purity ≥96%
  • MDL No. MFCD08688592
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₃BrClNO
  • Molecular Weight 208.44
  • Synonym(s) 5-BROMO-2-CHLORO-PYRIDIN-3-OL
  • SMILES Brc1cnc(c(c1)O)Cl

Description

5-Bromo-2-chloropyridin-3-ol is a halogenated pyridinol scaffold featuring bromo and chloro substituents at the 5- and 2-positions, respectively. This electron-deficient heterocycle integrates readily into cross-coupling reactions, serving as a key building block for pharmaceutical intermediates and functional materials. The phenolic hydroxyl group enhances reactivity in nucleophilic substitutions and enables derivatization under mild conditions.

Application

5-Bromo-2-chloropyridin-3-ol serves as a versatile building block in medicinal chemistry, enabling palladium-catalyzed cross-coupling reactions due to its orthogonal halogen reactivity. The bromo group facilitates Suzuki and Stille couplings, while the chloro and hydroxyl functionalities offer sites for further functionalization or protection. Its bench-stable crystalline form simplifies handling and purification, making it well-suited for modular synthesis of heterocyclic scaffolds and API intermediates.

Synthesis

  • Route1

    References

    • ABBOTT LABORATORIES Patent: EP1428824 A1, 2004 ; Location in patent: Page 37 ;
  • Route2

    References

    • Breteche, Anne; Marchand, Pascal; Nourrisson, Marie-Renee; Hautefaye, Patrick; De Nanteuil, Guillaume; Duflos, Muriel Tetrahedron, 2011 , vol. 67, # 26 p. 4767 - 4773
  • Route3
    • In-stock
      5-Bromo-3-pyridinol|CS-W019637
      74115-13-2
    • null|null
      7681-52-9
    • ~93%
    • In-stock
      5-Bromo-2-chloropyridin-3-ol|CS-W003542
      286946-77-8

    References

    • Schrimpf, Michael R.; Tietje, Karin R.; Toupence, Richard B.; Ji, Jianguo; Basha, Anwer; Bunnelle, William H.; Daanen, Jerome F.; Pace, Jennifer M.; Sippy, Kevin B. Patent: US2002/19388 A1, 2002 ;

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   33.12
  • LogP   2.2031
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   0

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