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CS-W001157 4
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4-Chloro-1H-indole-2-carboxylic acid

  • CAS No. 24621-73-6

  • Cat. No. CS-0054251
  • Purity≥96%
  • MDL No.None

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

4-Chloro-1H-indole-2-carboxylic acid|CS-0054251

Structure of 24621-73-6

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General Information

  • CAS No. 24621-73-6
  • Cat. No. CS-0054251
  • Purity ≥96%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₆ClNO₂
  • Molecular Weight 195.60
  • Synonym(s) 4-Chloroindole-2-carboxylic acid
  • SMILES OC(=O)C1=CC2=C(N1)C=CC=C2Cl

Description

4-Chloro-1H-indole-2-carboxylic acid features a chlorine-substituted indole core with a carboxylic acid group at the 2-position, offering enhanced electron-withdrawing character and improved solubility in polar solvents. This scaffold integrates readily into bioactive molecule design, particularly in medicinal chemistry applications involving heterocyclic scaffolds.

Application

4-Chloro-1H-indole-2-carboxylic acid serves as a versatile building block in medicinal chemistry, enabling direct incorporation into indole-based scaffolds via standard coupling reactions. Its carboxylic acid functionality facilitates amide, ester, and hydrazide formation under mild conditions, while the 4-chloro substituent provides a handle for palladium-catalyzed cross-coupling or nucleophilic aromatic substitution. The compound exhibits good bench stability and is readily purified by recrystallization, supporting efficient integration into multi-step syntheses of bioactive molecules.

Synthesis

  • Route1
    • 3-(2-Chloro-6-nitrophenyl)-2-oxopropanoic acid|CS-0511466
      36892-19-0
    • ~%
    • In-stock
      4-Chloro-1H-indole-2-carboxylic acid|CS-0054251
      24621-73-6

    References

    • Journal of the American Chemical Society, , vol. 71, p. 761,763
  • Route2

    References

    • Journal of Medicinal Chemistry, , vol. 31, # 5 p. 944 - 948

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   53.09
  • LogP   2.5195
  • H_Acceptors   1
  • H_Donors   2
  • Rotatable_Bonds   1

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