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CS-W001157 4
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5-Bromo-3-pyridinol

  • CAS No. 74115-13-2

  • Cat. No. CS-W019637
  • Purity≥97%
  • MDL No.MFCD00661305

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

5-Bromo-3-pyridinol|CS-W019637

Structure of 74115-13-2

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General Information

  • CAS No. 74115-13-2
  • Cat. No. CS-W019637
  • Purity ≥97%
  • MDL No. MFCD00661305
  • Storage 4°C, sealed storage, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₄BrNO
  • Molecular Weight 174.00
  • Synonym(s) None
  • SMILES OC1=CN=CC(Br)=C1

Description

5-Bromo-3-pyridinol features a bromine substituent at the 5-position and a hydroxyl group at the 3-position of the pyridine ring, creating a versatile scaffold for cross-coupling and functionalization. The electron-deficient heterocycle enables selective transformations under palladium catalysis, while the phenolic OH enhances solubility and facilitates derivatization. This bench-stable compound integrates readily into complex molecular architectures.

Application

5-Bromo-3-pyridinol serves as a versatile building block in medicinal chemistry, enabling direct functionalization at the 3-position of the pyridine ring. Its bromine substituent facilitates palladium-catalyzed cross-coupling reactions, while the phenolic hydroxyl group offers opportunities for derivatization or metal complexation. The compound exhibits good bench stability and is compatible with common protecting group strategies, making it well-suited for modular synthesis of heterocyclic scaffolds and pharmaceutical intermediates.

Synthesis

  • Route1

    References

    • Roche Palo Alto LLC Patent: US2004/198736 A1, 2004 ; Location in patent: Page/Page column 86 ;
  • Route2

    References

    • ABBOTT LABORATORIES Patent: EP1428824 A1, 2004 ; Location in patent: Page 37 ;
  • Route3

    References

    • Pfizer Inc Patent: US2009/170886 A1, 2009 ; Location in patent: Page/Page column 28 ;

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-P330-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   33.12
  • LogP   1.5497
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   0

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