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CS-W001157 4
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6-Chloro-2-iodopyridin-3-ol

  • CAS No. 188057-26-3

  • Cat. No. CS-W006358
  • Molecule weight255.44
  • Purity≥97%
  • MDL No.MFCD07636749

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

6-Chloro-2-iodopyridin-3-ol|CS-W006358

Structure of 188057-26-3

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General Information

  • CAS No. 188057-26-3
  • Cat. No. CS-W006358
  • Purity ≥97%
  • MDL No. MFCD07636749
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₃ClINO
  • Molecular Weight 255.44
  • Synonym(s) 6-Chloro-2-iodo-3-pyridinol
  • SMILES OC1=CC=C(Cl)N=C1I

Description

6-Chloro-2-iodopyridin-3-ol features a sterically accessible pyridin-3-ol core with complementary halogen handles: a chlorine at C6 and an iodine at C2. This arrangement enables selective cross-coupling reactions, particularly in late-stage functionalization of heterocyclic scaffolds. The phenolic hydroxyl group enhances solubility and provides a handle for derivatization, while the electron-deficient ring system supports efficient palladium-catalyzed transformations under standard conditions.

Application

6-Chloro-2-iodopyridin-3-ol serves as a versatile building block in medicinal chemistry, enabling palladium-catalyzed cross-coupling reactions due to its complementary halogen reactivity. The iodide group facilitates efficient C–C and C–heteroatom bond formation, while the chloro and hydroxyl substituents offer orthogonal functionalization potential. This compound exhibits bench stability and is compatible with standard purification methods, making it well-suited for modular synthesis of bioactive heterocycles and API intermediates.

Synthesis

  • Route1

    References

    • Eli Lilly and Company Patent: US6696439 B1, 2004 ; Location in patent: Page column 20 ; US 6696439 B1
  • Route2

    References

    • US6001849 A1, ;
  • Route3

    References

    • Tetrahedron Letters, , vol. 44, # 4 p. 725 - 728

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   2.0452
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   0

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