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

  • CAS No. 399-68-8

  • Cat. No. CS-W005389
  • Purity≥98%
  • MDL No.MFCD02664471

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

4-Fluoro-1H-indole-2-carboxylic acid|CS-W005389

Structure of 399-68-8

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General Information

  • CAS No. 399-68-8
  • Cat. No. CS-W005389
  • Purity ≥98%
  • MDL No. MFCD02664471
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₆FNO₂
  • Molecular Weight 179.15
  • Synonym(s) 4-Fluoroindole-2-carboxylic acid
  • SMILES O=C(C(N1)=CC2=C1C=CC=C2F)O

Description

4-Fluoro-1H-indole-2-carboxylic acid features a fluorinated indole core with a carboxylic acid group at the 2-position, enabling direct incorporation into bioactive molecule scaffolds. The electron-withdrawing fluorine substituent enhances metabolic stability and modulates electronic properties for medicinal chemistry applications. This bench-stable derivative serves as a key building block in the synthesis of targeted therapeutics and functionalized heterocycles.

Application

4-Fluoro-1H-indole-2-carboxylic acid serves as a versatile building block for the synthesis of bioactive indole derivatives, particularly in medicinal chemistry and agrochemical research. The molecule combines a fluorinated aromatic ring with a carboxylic acid group, enabling direct coupling reactions, amide formation, and derivatization under standard conditions. Its bench-stable nature and compatibility with common protecting group strategies facilitate efficient access to complex heterocyclic scaffolds.

Synthesis

  • Route1
    • null|null
      7593-91-1
    • ~62%
    • In-stock
      4-Fluoro-1H-indole-2-carboxylic acid|CS-W005389
      399-68-8

    References

    • Fagan, Gay P.; Chapleo, Christopher B.; Lane, Anthony C.; Myers, Malcolm; Roach, Alan G.; et al Journal of Medicinal Chemistry, 1988 , vol. 31, # 5 p. 944 - 948
  • Route2

    References

    • Bozilovic, Jelena; Engels, Joachim W. Nucleosides, Nucleotides and Nucleic Acids, 2007 , vol. 26, # 8-9 p. 869 - 871
  • Route3

    References

    • Genentech, Inc.; Array BioPharma Inc.; Blake, Jim; Chen, Huifen; Chicarelli, Mark; Gaudino, John; Gazzard, Lewis; Kintz, Sam; Mohr, Pete; Robarge, Kirk; Schwarz, Jacob; Zhou, Aihe Patent: US2014/66453 A1, 2014 ;

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

Quality Control

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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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