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CS-W001157 4
Total: USD 88.00

6-Bromo-1H-indole-3-carboxylic acid

  • CAS No. 101774-27-0

  • Cat. No. CS-W004920
  • Purity≥95%
  • MDL No.MFCD05664008

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

6-Bromo-1H-indole-3-carboxylic acid|CS-W004920

Structure of 101774-27-0

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General Information

  • CAS No. 101774-27-0
  • Cat. No. CS-W004920
  • Purity ≥95%
  • MDL No. MFCD05664008
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₆BrNO₂
  • Molecular Weight 240.06
  • Synonym(s) None
  • SMILES BrC1=CC2=C(C(C(O)=O)=CN2)C=C1

Description

6-Bromo-1H-indole-3-carboxylic acid features a brominated indole core with a carboxylic acid group at the 3-position, enabling direct coupling in pharmaceutical and agrochemical synthesis. The electron-deficient aromatic system enhances reactivity in transition-metal-catalyzed transformations, while the bench-stable functionality simplifies handling under standard conditions.

Application

6-Bromo-1H-indole-3-carboxylic acid serves as a versatile building block for the synthesis of functionalized indole scaffolds. Its bromine substituent enables palladium-catalyzed cross-coupling reactions, while the carboxylic acid group facilitates amide formation, esterification, and direct derivatization. The compound exhibits good bench stability and is compatible with standard purification methods, making it well-suited for medicinal chemistry campaigns and API intermediate development.

Synthesis

  • Route1

    References

    • FENG, Yangbo; CHEN, Yen Ting; SESSIONS, Hampton; MISHRA, Jitendra K.; CHOWDHURY, Sarwat; YIN, Yan; LOGRASSO, Philip; LUO, Jun-Li; BANNISTER, Thomas; SCHROETER, Thomas Patent: WO2011/50245 A1, 2011 ; Location in patent: Page/Page column 81 ; WO 2011/050245 A1
  • Route2

    References

    • ELI LILLY AND COMPANY Patent: WO2009/12125 A1, 2009 ; Location in patent: Page/Page column 60-61 ;
  • Route3

    References

    • Bioorganic and Medicinal Chemistry Letters, , vol. 21, # 23 p. 7107 - 7112

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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