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3-Iodo-1H-pyridin-2-one

  • CAS No. 111079-46-0

  • Cat. No. CS-0060372
  • Purity≥98%
  • MDL No.None

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

3-Iodo-1H-pyridin-2-one|CS-0060372

Structure of 111079-46-0

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General Information

  • CAS No. 111079-46-0
  • Cat. No. CS-0060372
  • Purity ≥98%
  • MDL No. None
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₄INO
  • Molecular Weight 221.00
  • Synonym(s) 3-Iodopyridin-2(1H)-one
  • SMILES C1=CC(=C(N=C1)O)I

Description

3-Iodo-1H-pyridin-2-one features a reactive iodine handle at the C3 position of a pyridinone scaffold, enabling direct coupling in cross-coupling reactions. The electron-deficient ring system enhances reactivity in palladium-catalyzed transformations, while the bench-stable nature supports reliable handling under standard conditions. This compound serves as a key building block for functionalized heterocycles in medicinal chemistry and materials science.

Application

3-Iodo-1H-pyridin-2-one serves as a versatile building block in medicinal chemistry, enabling palladium-catalyzed cross-coupling reactions to construct biologically relevant heterocyclic scaffolds. The iodide group provides high reactivity in Suzuki, Stille, and Negishi couplings, while the pyridinone core offers hydrogen-bonding capability and metabolic stability. Its bench-stable nature and compatibility with diverse functional groups facilitate efficient synthesis of drug candidates and macrocyclic compounds.

Synthesis

  • Route1

    References

    • Malamas, Michael S.; Sredy, Janet; Moxham, Christopher; Katz, Alan; Xu, Weixin; McDevitt, Robert; Adebayo, Folake O.; Sawicki, Diane R.; Seestaller, Laura; Sullivan, Donald; Taylor, Joseph R. Journal of Medicinal Chemistry, 2000 , vol. 43, # 7 p. 1293 - 1310

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   1.3918
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   0

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