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CS-W001157 4
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6-Chloro-1H-indole-3-carboxylic acid

  • CAS No. 766557-02-2

  • Cat. No. CS-W019457
  • Purity≥98%
  • MDL No.MFCD07776607

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

6-Chloro-1H-indole-3-carboxylic acid|CS-W019457

Structure of 766557-02-2

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General Information

  • CAS No. 766557-02-2
  • Cat. No. CS-W019457
  • Purity ≥98%
  • MDL No. MFCD07776607
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₆ClNO₂
  • Molecular Weight 195.60
  • Synonym(s) 6-CHLOROINDOLE-3-CARBOXYLIC ACID
  • SMILES O=C(C1=CNC2=C1C=CC(Cl)=C2)O

Description

6-Chloro-1H-indole-3-carboxylic acid integrates a chlorine substituent at the 6-position of the indole core, enhancing electronic properties for synthetic applications. This bench-stable carboxylic acid derivative serves as a key building block in medicinal chemistry and materials science, enabling direct coupling reactions without protection.

Application

6-Chloro-1H-indole-3-carboxylic acid serves as a versatile building block in medicinal chemistry, enabling direct incorporation into indole-based scaffolds common in kinase inhibitors and CNS-active compounds. The carboxylic acid group facilitates straightforward amide coupling, esterification, or derivatization under standard conditions. Its chloro substituent at the 6-position provides moderate electron-withdrawing character and enhances metabolic stability, while maintaining bench stability and compatibility with diverse reaction environments.

Synthesis

  • Route1
    • 1-(6-Chloro-1H-indol-3-yl)-2,2,2-trifluoroethan-1-one|CS-0454853
      676477-10-4
    • ~96%
    • In-stock
      6-Chloro-1H-indole-3-carboxylic acid|CS-W019457
      766557-02-2

    References

    • Bissantz, Caterina; Grundschober, Christophe; Ratni, Hasane; Rogers-Evans, Mark; Schnider, Patrick Patent: US2007/72888 A1, 2007 ; Location in patent: Page/Page column 14-15 ; US 20070072888 A1
  • Route2

    References

    • Bissantz, Caterina; Grundschober, Christophe; Ratni, Hasane; Rogers-Evans, Mark; Schnider, Patrick Patent: US2007/155761 A1, 2007 ; Location in patent: Page/Page column 14 ; US 20070155761 A1
  • Route3

    References

    • CrystEngComm, , vol. 15, # 37 p. 7490 - 7497

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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