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5-Bromo-7-ethyl-1H-indazole

  • CAS No. 635712-49-1

  • Cat. No. CS-0096453
  • Purity≥97%
  • MDL No.MFCD11044594

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

5-Bromo-7-ethyl-1H-indazole|CS-0096453

Structure of 635712-49-1

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General Information

  • CAS No. 635712-49-1
  • Cat. No. CS-0096453
  • Purity ≥97%
  • MDL No. MFCD11044594
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₉BrN₂
  • Molecular Weight 225.09
  • Synonym(s) 1h-indazole,5-bromo-7-ethyl
  • SMILES CCC1=CC(Br)=CC2=C1NN=C2

Description

5-Bromo-7-ethyl-1H-indazole is a halogenated indazole derivative featuring a bromine atom at the 5-position and an ethyl group at the 7-position, enabling selective functionalization in synthetic transformations. This electron-deficient heterocycle serves as a key scaffold for pharmaceutical intermediates and bioactive molecule development, offering enhanced metabolic stability and favorable solubility profiles under standard reaction conditions.

Application

5-Bromo-7-ethyl-1H-indazole serves as a versatile building block in medicinal chemistry, enabling palladium-catalyzed cross-coupling reactions due to its well-defined bromine handle. The ethyl group at the 7-position enhances solubility and modulates electronic properties, while the indazole core provides a stable, bioisosteric scaffold for drug discovery. Bench-stable and amenable to standard purification techniques, it facilitates efficient synthesis of complex heterocyclic systems.

Synthesis

  • Route1
    • null|null
      943145-76-4
    • ~82%
    • In-stock
      5-Bromo-7-ethyl-1H-indazole|CS-0096453
      635712-49-1

    References

    • BRISTOL-MYERS SQUIBB COMPANY Patent: WO2003/104236 A1, 2003 ; Location in patent: Page 127 ; WO 03/104236 A1
  • Route2
    • 4-Bromo-2-ethyl-6-methylaniline|CS-0191142
      70598-49-1
    • ~32%
    • 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

    • Freeman-Cook, Kevin D.; Amor, Paul; Bader, Scott; Buzon, Leanne M.; Coffey, Steven B.; Corbett, Jeffrey W.; Dirico, Kenneth J.; Doran, Shawn D.; Elliott, Richard L.; Esler, William; Guzman-Perez, Angel; Henegar, Kevin E.; Houser, Janet A.; Jones, Christopher S.; Limberakis, Chris; Loomis, Katherine; McPherson, Kirk; Murdande, Sharad; Nelson, Kendra L.; Phillion, Dennis; Pierce, Betsy S.; Song, Wei; Sugarman, Eliot; Tapley, Susan; Tu, Meihua; Zhao, Zhengrong Journal of Medicinal Chemistry, 2012 , vol. 55, # 2 p. 935 - 942
  • Route3

    References

    • Freeman-Cook, Kevin D.; Amor, Paul; Bader, Scott; Buzon, Leanne M.; Coffey, Steven B.; Corbett, Jeffrey W.; Dirico, Kenneth J.; Doran, Shawn D.; Elliott, Richard L.; Esler, William; Guzman-Perez, Angel; Henegar, Kevin E.; Houser, Janet A.; Jones, Christopher S.; Limberakis, Chris; Loomis, Katherine; McPherson, Kirk; Murdande, Sharad; Nelson, Kendra L.; Phillion, Dennis; Pierce, Betsy S.; Song, Wei; Sugarman, Eliot; Tapley, Susan; Tu, Meihua; Zhao, Zhengrong Journal of Medicinal Chemistry, 2012 , 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   2.8878
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   1

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