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CS-W001157 4
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3-Iodo-2-nitropyridine

  • CAS No. 54231-34-4

  • Cat. No. CS-0041449
  • Molecule weight249.99
  • Purity≥98%
  • MDL No.MFCD08061318

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

3-Iodo-2-nitropyridine|CS-0041449

Structure of 54231-34-4

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General Information

  • CAS No. 54231-34-4
  • Cat. No. CS-0041449
  • Purity ≥98%
  • MDL No. MFCD08061318
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₃IN₂O₂
  • Molecular Weight 249.99
  • Synonym(s) 2-Nitro-3-jodpyridin
  • SMILES O=[N+](C1=NC=CC=C1I)[O-]

Description

3-Iodo-2-nitropyridine features a nitro group at the 2-position and an iodine atom at the 3-position, creating a highly reactive site for cross-coupling transformations. This electron-deficient pyridine scaffold enables efficient palladium-catalyzed reactions, delivering functionalized heterocycles with high regiocontrol. The compound exhibits stability under standard bench conditions and serves as a key building block in medicinal chemistry and materials science.

Application

3-Iodo-2-nitropyridine serves as a versatile building block in cross-coupling chemistry, enabling efficient access to substituted pyridines via palladium-catalyzed reactions. The iodide group facilitates reliable C–C and C–heteroatom bond formation, while the ortho-nitro group provides a handle for selective reduction and subsequent heterocycle elaboration. Its bench-stable nature and compatibility with diverse functional groups make it a practical choice for medicinal chemistry and process development workflows.

Synthesis

  • Route1

    References

    • Patriciu, Oana-Irina; Finaru, Adriana-Luminita; Massip, Stephane; Leger, Jean-Michel; Jarry, Christian; Guillaumet, Gerald European Journal of Organic Chemistry, 2009 , # 22 p. 3753 - 3764

Safety Information

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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   56.03
  • LogP   1.5944
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   1

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