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CS-W001157 4
Total: USD 88.00

4-Iodo-1H-pyrrolo[2,3-b]pyridine

  • CAS No. 319474-34-5

  • Cat. No. CS-0003993
  • Molecule weight244.03
  • Purity≥96%
  • MDL No.MFCD08272234

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

4-Iodo-1H-pyrrolo[2,3-b]pyridine|CS-0003993

Structure of 319474-34-5

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General Information

  • CAS No. 319474-34-5
  • Cat. No. CS-0003993
  • Purity ≥96%
  • MDL No. MFCD08272234
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₅IN₂
  • Molecular Weight 244.03
  • Synonym(s) 4-Iod-1H-pyrrolo[2,3-b]pyridin
  • SMILES IC1=C2C(NC=C2)=NC=C1

Description

4-Iodo-1H-pyrrolo[2,3-b]pyridine features a fused heterocyclic core with a strategically positioned iodine atom enabling direct functionalization in cross-coupling reactions. This electron-deficient scaffold integrates readily into complex molecular architectures, offering enhanced stability under standard conditions for synthetic applications in medicinal chemistry and materials science.

Application

4-Iodo-1H-pyrrolo[2,3-b]pyridine serves as a versatile building block for constructing biologically relevant heterocycles via palladium-catalyzed cross-coupling reactions. The iodide group enables reliable Suzuki, Stille, and Negishi couplings, while the pyrrolopyridine core provides a rigid, electron-deficient scaffold suitable for medicinal chemistry applications. Bench-stable and readily purified by flash chromatography, it functions effectively in multi-step synthesis workflows requiring functional group tolerance and predictable reactivity.

Synthesis

  • Route1

    References

    • Caldwell, John J.; Cheung, Kwai-Ming; Collins, Ian Tetrahedron Letters, 2007 , vol. 48, # 9 p. 1527 - 1529
  • Route2
    • 1-(4-iodo-1H-pyrrolo[2,3-b]pyridin-1-yl)ethan-1-one|CS-0004787
      443729-67-7
    • ~94%
    • In-stock
      4-Iodo-1H-pyrrolo[2,3-b]pyridine|CS-0003993
      319474-34-5

    References

    • Riken; TagCyx Biotechnologies Patent: EP2487180 A1, 2012 ; Location in patent: Page/Page column 20 ;
  • Route3
    • null|null
      75-36-5
    • In-stock
      4-Chloro-7-azaindole|CS-B0097
      55052-28-3
    • ~0%
    • In-stock
      4-Iodo-1H-pyrrolo[2,3-b]pyridine|CS-0003993
      319474-34-5
    • 1-(4-iodo-1H-pyrrolo[2,3-b]pyridin-1-yl)ethan-1-one|CS-0004787
      443729-67-7

    References

    • Riken; TagCyx Biotechnologies Patent: EP2487180 A1, 2012 ; Location in patent: Page/Page column 20 ;

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS05,GHS07
Signal Word : Danger
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H318-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P362-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   28.68
  • LogP   2.1675
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   0

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