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6-Chloro-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid

  • CAS No. 800402-07-7

  • Cat. No. CS-0002366
  • Molecule weight196.59
  • Purity≥95%
  • MDL No.MFCD09878690

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

6-Chloro-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid|CS-0002366

Structure of 800402-07-7

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General Information

  • CAS No. 800402-07-7
  • Cat. No. CS-0002366
  • Purity ≥95%
  • MDL No. MFCD09878690
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₅ClN₂O₂
  • Molecular Weight 196.59
  • Synonym(s) acide 6-chloro-1H-pyrrolo[2,3-b]pyridine-2-carboxylique
  • SMILES O=C(O)C1=CC2=CC=C(Cl)N=C2N1

Description

6-Chloro-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid features a fused heterocyclic core with orthogonal electron-withdrawing chlorine and carboxylic acid functionalities. This combination enables direct incorporation into bioactive molecule scaffolds, particularly in kinase inhibitors and medicinal chemistry libraries. The carboxylic acid group supports derivatization via amide or ester formation, while the chlorinated pyrrolopyridine framework provides metabolic stability and enhanced binding affinity through π-stacking interactions.

Application

6-Chloro-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid serves as a versatile building block for the synthesis of bioactive heterocycles, enabling efficient functionalization at the pyrrole nitrogen and carboxylic acid terminus. Its well-defined reactivity facilitates coupling reactions, cyclizations, and derivatization under standard conditions, offering robust bench stability and compatibility with diverse synthetic workflows in medicinal chemistry and API development.

Synthesis

  • Route1

    References

    • WO2011/71725 A1, ; WO 2011/071725 A1
  • Route2
    • N-(6-Chloro-3-iodopyridin-2-yl)pivalamide|CS-0612973
      800402-05-5
    • ~%
    • In-stock
      6-Chloro-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid|CS-0002366
      800402-07-7

    References

    • WO2011/71725 A1, ; WO 2011/071725 A1
  • Route3

    References

    • WO2011/71725 A1, ; WO 2011/071725 A1

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

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Computational Chemistry Data

  • TPSA   65.98
  • LogP   1.9145
  • H_Acceptors   2
  • H_Donors   2
  • Rotatable_Bonds   1

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