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CS-W001157 4
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6-Fluoroindole-2-carboxylic acid

  • CAS No. 3093-97-8

  • Cat. No. CS-W001533
  • Purity≥98%
  • MDL No.MFCD01863162

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

6-Fluoroindole-2-carboxylic acid|CS-W001533

Structure of 3093-97-8

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General Information

  • CAS No. 3093-97-8
  • Cat. No. CS-W001533
  • Purity ≥98%
  • MDL No. MFCD01863162
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₆FNO₂
  • Molecular Weight 179.15
  • Synonym(s) 1H-6-FLUOROINDOLE-2-CARBOXYLIC ACID
  • SMILES Fc1ccc2c(c1)[nH]c(c2)C(=O)O

Description

6-Fluoroindole-2-carboxylic acid features a fluorinated indole core with a carboxylic acid group at the 2-position, enabling direct incorporation into bioactive scaffolds. The electron-withdrawing fluorine at the 6-position enhances metabolic stability and modulates electronic properties for medicinal chemistry applications. This bench-stable derivative supports efficient synthesis of targeted heterocycles and functionalized peptides.

Application

6-Fluoroindole-2-carboxylic acid serves as a versatile building block for medicinal chemistry and heterocyclic synthesis, enabling direct incorporation of fluorinated indole scaffolds into bioactive molecules. Its carboxylic acid functionality facilitates amide bond formation, esterification, and coupling reactions under standard conditions. The fluorine substituent enhances metabolic stability and modulates electronic properties, while the indole core provides a rigid, planar structure suitable for target engagement in kinase inhibitors and CNS-active compounds. Bench-stable and readily purified by recrystallization, it functions reliably in both small-molecule discovery and process-scale applications.

Synthesis

  • Route1

    References

    • Zhang, Fan; Zhao, Yanfang; Sun, Li; Ding, Lu; Gu, Yucheng; Gong, Ping European Journal of Medicinal Chemistry, 2011 , vol. 46, # 7 p. 3149 - 3157
  • Route2

    References

    • Bozilovic, Jelena; Engels, Joachim W. Nucleosides, Nucleotides and Nucleic Acids, 2007 , vol. 26, # 8-9 p. 869 - 871
  • Route3
    • p-Fluorobenzenecarboxaldehyde Atorvastatin calcium|CS-0214005
      459-57-4
    • ~%
    • In-stock
      6-Fluoroindole-2-carboxylic acid|CS-W001533
      3093-97-8

    References

    • Journal of Medicinal Chemistry, , vol. 43, # 24 p. 4701 - 4710

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   2.0052
  • H_Acceptors   1
  • H_Donors   2
  • Rotatable_Bonds   1

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