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CS-W001157 4
Total: USD 88.00

5-Bromo-2-iodopyridin-3-ol

  • CAS No. 188057-49-0

  • Cat. No. CS-0037912
  • Purity≥96%
  • MDL No.None

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

5-Bromo-2-iodopyridin-3-ol|CS-0037912

Structure of 188057-49-0

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General Information

  • CAS No. 188057-49-0
  • Cat. No. CS-0037912
  • Purity ≥96%
  • MDL No. None
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₃BrINO
  • Molecular Weight 299.89
  • Synonym(s) 5-Bromo-2-iodo-3-pyridinol
  • SMILES C1=C(C=NC(=C1O)I)Br

Description

5-Bromo-2-iodopyridin-3-ol features a pyridin-3-ol core substituted with bromo and iodo groups at the 5- and 2-positions, respectively. This electron-deficient heterocycle enables direct functionalization in cross-coupling reactions. The phenolic hydroxyl group enhances solubility and provides a handle for derivatization. Bench-stable under standard conditions, it serves as a key building block in medicinal chemistry and materials synthesis.

Application

5-Bromo-2-iodopyridin-3-ol serves as a versatile building block for late-stage functionalization and cross-coupling reactions in medicinal chemistry. Its dual halogenation pattern enables sequential Pd-catalyzed couplings with high chemoselectivity, while the phenolic hydroxyl group supports derivatization and metal coordination. The compound exhibits excellent bench stability and facilitates purification via recrystallization, making it well-suited for scalable synthesis of heterocyclic scaffolds and API intermediates.

Synthesis

  • Route1

    References

    • GLAXO GROUP LIMITED Patent: WO2008/128961 A1, 2008 ; Location in patent: Page/Page column 27; 75-76 ; WO 2008/128961 A1
  • Route2

    References

    • Bioorganic and Medicinal Chemistry Letters, , vol. 23, # 24 p. 6784 - 6788
  • Route3

    References

    • Bioorganic and Medicinal Chemistry Letters, , vol. 23, # 24 p. 6784 - 6788

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   2.1543
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   0

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