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CS-W001157 4
Total: USD 88.00

5-Bromo-3,7-dimethyl-1H-indazole

  • CAS No. 1031417-71-6

  • Cat. No. CS-0096443
  • Purity≥97%
  • MDL No.MFCD12755762

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

5-Bromo-3,7-dimethyl-1H-indazole|CS-0096443

Structure of 1031417-71-6

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General Information

  • CAS No. 1031417-71-6
  • Cat. No. CS-0096443
  • Purity ≥97%
  • MDL No. MFCD12755762
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₉BrN₂
  • Molecular Weight 225.09
  • Synonym(s) 5-bromo-3,7-dimethyl-2H-indazole
  • SMILES CC1=CC(Br)=CC2=C1NN=C2C

Description

5-Bromo-3,7-dimethyl-1H-indazole delivers a sterically hindered, electron-deficient heterocyclic scaffold ideal for transition-metal-catalyzed coupling reactions. The bromine at the 5-position enables direct functionalization, while the methyl groups at C3 and C7 enhance solubility and stability under standard conditions. This compound serves as a key building block in medicinal chemistry and materials science.

Application

5-Bromo-3,7-dimethyl-1H-indazole serves as a versatile building block in medicinal chemistry, enabling direct functionalization at the bromine site via palladium-catalyzed cross-coupling reactions. The methyl groups at C3 and C7 enhance metabolic stability and modulate electronic properties, while the indazole core provides a rigid, hydrogen-bonding scaffold suitable for target engagement. Bench-stable and readily purified by chromatography, it facilitates efficient access to diverse heterocyclic architectures in API development workflows.

Synthesis

  • Route1
    • 4-Bromo-2-ethyl-6-methylaniline|CS-0191142
      70598-49-1
    • ~25%
    • In-stock
      5-Bromo-7-ethyl-1H-indazole|CS-0096453
      635712-49-1
    • In-stock
      5-Bromo-3,7-dimethyl-1H-indazole|CS-0096443
      1031417-71-6

    References

    • WO2008/65508 A1, ; Page/Page column 31 ;
  • Route2

    References

    • Journal of Medicinal Chemistry, , vol. 55, # 2 p. 935 - 942

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   28.68
  • LogP   2.94224
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   0

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