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CS-W001157 4
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3-Bromo-1H-indazole-5-carbonitrile

  • CAS No. 395101-67-4

  • Cat. No. CS-0042024
  • Purity≥97%
  • MDL No.MFCD09263218

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

3-Bromo-1H-indazole-5-carbonitrile|CS-0042024

Structure of 395101-67-4

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General Information

  • CAS No. 395101-67-4
  • Cat. No. CS-0042024
  • Purity ≥97%
  • MDL No. MFCD09263218
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₄BrN₃
  • Molecular Weight 222.04
  • Synonym(s) 3-BROMO-5-CYANO (1H)INDAZOLE
  • SMILES N#CC1=CC2=C(NN=C2Br)C=C1

Description

3-Bromo-1H-indazole-5-carbonitrile features a bromine substituent at the 3-position and a nitrile group at the 5-position of the indazole core, creating a bifunctional scaffold with enhanced reactivity for cross-coupling and bioconjugation. The electron-deficient aromatic system facilitates transition metal-catalyzed transformations, while the nitrile group offers synthetic versatility in amide and heterocycle formation. This compound serves as a key intermediate in medicinal chemistry and materials science applications.

Application

3-Bromo-1H-indazole-5-carbonitrile serves as a versatile building block for the synthesis of heterocyclic scaffolds in medicinal chemistry. The molecule combines a bromo substituent for palladium-catalyzed cross-coupling reactions with a nitrile group amenable to hydrolysis or cyclization, enabling access to diverse indazole-based pharmacophores. Its bench-stable nature and compatibility with standard reaction conditions facilitate efficient downstream functionalization.

Synthesis

  • Route1

    References

    • EP2489663 A1, ; Paragraph 0215; 0216 ; EP 2489663 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   52.47
  • LogP   2.19708
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   0

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