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CS-W001157 4
Total: USD 88.00

1H-Imidazo[4,5-b]pyridine

  • CAS No. 273-21-2

  • Cat. No. CS-0018962
  • Purity≥98%
  • MDL No.MFCD13176755

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

1H-Imidazo[4,5-b]pyridine|CS-0018962

Structure of 273-21-2

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General Information

  • CAS No. 273-21-2
  • Cat. No. CS-0018962
  • Purity ≥98%
  • MDL No. MFCD13176755
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₅N₃
  • Molecular Weight 119.12
  • Synonym(s) 4-Azabenzimidazole; 7-Azabenzimidazole; NSC 403091
  • SMILES C12=NC=CC=C1N=CN2

Description

1H-Imidazo[4,5-b]pyridine is a rigid, electron-rich heterocycle featuring a fused imidazole-pyridine core. This scaffold exhibits strong π-conjugation and planarity, enabling effective integration into advanced materials and pharmaceutical scaffolds. The nitrogen-rich framework enhances solubility in polar solvents and supports metal coordination. Its bench-stable nature facilitates handling under standard laboratory conditions.

Application

1H-Imidazo[4,5-b]pyridine serves as a versatile heterocyclic scaffold in medicinal chemistry, enabling efficient access to biologically active compounds through established functionalization at the 2-, 4-, and 5-positions. Its inherent stability and compatibility with standard coupling reactions facilitate rapid diversification, while its planar structure supports favorable π–π interactions in target binding. This core functions effectively in parallel synthesis campaigns and scale-up processes, offering robust performance in amide bond formation, Suzuki-Miyaura coupling, and electrophilic substitution.

Synthesis

  • Route1
    • In-stock
      Pyridine, 2,3-diamino-|CS-D1498
      452-58-4
    • null|null
      122-51-0
    • ~89%
    • In-stock
      1H-Imidazo[4,5-b]pyridine|CS-0018962
      273-21-2

    References

    • Montazeri, Naser; Esmaeili, Abbas Asian Journal of Chemistry, 2013 , vol. 25, # 6 p. 3446 - 3448
  • Route2
    • In-stock
      Pyridine, 2,3-diamino-|CS-D1498
      452-58-4
    • null|null
      124-38-9
    • ~72%
    • In-stock
      1H-Imidazo[4,5-b]pyridine|CS-0018962
      273-21-2

    References

    • Jacquet, Olivier; DasNevesGomes, Christophe; Ephritikhine, Michel; Cantat, Thibault ChemCatChem, 2013 , vol. 5, # 1 p. 117 - 120
  • Route3

    References

    • Vaughan et al. Journal of the American Chemical Society, 1949 , vol. 71, p. 1885

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
Precautionary Statements : P264-P270-P330-P501

Quality Control

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Computational Chemistry Data

  • TPSA   41.57
  • LogP   0.9579
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   0

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