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CS-W001157 4
Total: USD 88.00

3-bromo-5-chloropyridin-2-ol

  • CAS No. 137628-16-1

  • Cat. No. CS-W000824
  • Purity≥98%
  • MDL No.None

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

3-bromo-5-chloropyridin-2-ol|CS-W000824

Structure of 137628-16-1

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General Information

  • CAS No. 137628-16-1
  • Cat. No. CS-W000824
  • Purity ≥98%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₃BrClNO
  • Molecular Weight 208.44
  • Synonym(s) 3-Bromo-5-chloro-2-hydroxypyridine
  • SMILES Oc1ncc(Cl)cc1Br

Description

3-Bromo-5-chloropyridin-2-ol features a pyridine core functionalized with bromo and chloro substituents at the 3- and 5-positions, respectively, and a hydroxyl group at the 2-position. This arrangement delivers a polar, electron-deficient heterocycle ideal for palladium-catalyzed cross-coupling reactions. The ortho-hydroxyl group enables intramolecular coordination, enhancing reactivity in transition metal-mediated transformations. The molecule exhibits bench-stable handling characteristics under standard conditions.

Application

3-Bromo-5-chloropyridin-2-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, Stille, and Negishi couplings, while the chloro and hydroxyl functionalities offer sites for further functionalization or serve as directing groups. Its bench-stable nature and compatibility with diverse reaction conditions make it suitable for iterative synthesis of complex heterocyclic scaffolds and API intermediates.

Synthesis

  • Route1

    References

    • ALMIRALL PRODESFARMA S.A. Patent: WO2004/72037 A1, 2004 ; Location in patent: Page 11 ;
  • Route2

    References

    • Murtiashaw, Charles W.; Breitenbach, Ralph; Goldstein, Steven W.; Pezullo, Susan L.; Quallich, George J.; Sarges, Reinhard Journal of Organic Chemistry, 1992 , vol. 57, # 6 p. 1930 - 1933
  • Route3

    References

    • Journal of Organic Chemistry, , vol. 57, # 6 p. 1930 - 1933

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

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