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CS-W001157 4
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5-Bromo-1H-indole-3-carboxylic acid

  • CAS No. 10406-06-1

  • Cat. No. CS-W003237
  • Purity≥96%
  • MDL No.MFCD05664007

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

5-Bromo-1H-indole-3-carboxylic acid|CS-W003237

Structure of 10406-06-1

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General Information

  • CAS No. 10406-06-1
  • Cat. No. CS-W003237
  • Purity ≥96%
  • MDL No. MFCD05664007
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₆BrNO₂
  • Molecular Weight 240.06
  • Synonym(s) 5-BroMo-3-indolecarboxylic Acid
  • SMILES O=C(C1=CNC2=C1C=C(Br)C=C2)O

Description

5-Bromo-1H-indole-3-carboxylic acid features a bromine substituent at the 5-position of the indole core, enhancing electrophilic reactivity and enabling downstream functionalization. The carboxylic acid group provides a handle for amide coupling or esterification under standard conditions. This bench-stable compound serves as a key intermediate in medicinal chemistry and materials synthesis, particularly for heterocyclic systems requiring halogenated aromatic scaffolds.

Application

5-Bromo-1H-indole-3-carboxylic acid serves as a versatile building block for the synthesis of indole-based pharmaceuticals and functional materials. The bromo group enables palladium-catalyzed cross-coupling reactions, while the carboxylic acid facilitates amide formation, esterification, or direct derivatization. Its stability under standard bench conditions and compatibility with common protecting group strategies make it well-suited for iterative synthetic sequences in medicinal chemistry and process development.

Synthesis

  • Route1

    References

    • UNIVERSITE JOSEPH FOURIER; DENIS, Jean-Noël; JOLIVALT, Claude, Marcelle; MAURIN, Max, Maurin, Louis; JEANTY, Matthieu Patent: WO2013/14102 A1, 2013 ; Location in patent: Page/Page column 26; 30; 31 ;
  • Route2
    • In-stock
      5-Bromoindole|CS-D0617
      10075-50-0
    • null|null
      124-38-9
    • ~95%
    • In-stock
      5-Bromo-1H-indole-3-carboxylic acid|CS-W003237
      10406-06-1

    References

    • Yoo, Woo-Jin; Capdevila, Montse Guiteras; Du, Xiangwei; Kobayashi, Shu Organic Letters, 2012 , vol. 14, # 20 p. 5326 - 5329,4
  • Route3

    References

    • US2012/277205 A1, ; US 20120277205 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   53.09
  • LogP   2.6286
  • H_Acceptors   1
  • H_Donors   2
  • Rotatable_Bonds   1

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