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

  • CAS No. 660823-36-9

  • Cat. No. CS-0005441
  • Purity≥97%
  • MDL No.MFCD05663977

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

6-Bromo-1H-indazole-3-carboxylic acid|CS-0005441

Structure of 660823-36-9

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General Information

  • CAS No. 660823-36-9
  • Cat. No. CS-0005441
  • Purity ≥97%
  • MDL No. MFCD05663977
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₅BrN₂O₂
  • Molecular Weight 241.04
  • Synonym(s) 6-Bromoindazole-3-carboxylic acid
  • SMILES O=C(O)C1=NNC2=C1C=CC(Br)=C2

Description

6-Bromo-1H-indazole-3-carboxylic acid features a brominated indazole core paired with a carboxylic acid group at the 3-position, enabling direct conjugation in synthetic transformations. This electron-deficient heterocycle integrates readily into pharmaceutical intermediates and bioactive scaffolds, offering enhanced reactivity in cross-coupling and derivatization processes under standard conditions.

Application

6-Bromo-1H-indazole-3-carboxylic acid serves as a versatile building block for the synthesis of biologically active heterocycles and pharmaceutical intermediates. The bromine at the 6-position enables palladium-catalyzed cross-coupling reactions, while the carboxylic acid group facilitates derivatization via amide formation or esterification. Its bench-stable nature and compatibility with standard synthetic protocols make it ideal for medicinal chemistry campaigns requiring rapid diversification of indazole scaffolds.

Synthesis

  • Route1

    References

    • Schumacher, Richard; Danca, Mihaela Diana; Ma, Jianguo; Herbert, Brian; Nguyen, True Minh; Xie, Wenge; Tehim, Ashok Patent: US2007/78147 A1, 2007 ; Location in patent: Page/Page column 63 ;

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   65.98
  • LogP   2.0236
  • H_Acceptors   2
  • H_Donors   2
  • Rotatable_Bonds   1

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