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CS-W001157 4
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5-Bromo-6-nitro-1H-indazole

  • CAS No. 71785-49-4

  • Cat. No. CS-0038454
  • Purity≥97%
  • MDL No.MFCD09027584

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

5-Bromo-6-nitro-1H-indazole|CS-0038454

Structure of 71785-49-4

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General Information

  • CAS No. 71785-49-4
  • Cat. No. CS-0038454
  • Purity ≥97%
  • MDL No. MFCD09027584
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₄BrN₃O₂
  • Molecular Weight 242.03
  • Synonym(s) 1H-Indazole, 5-bromo-6-nitro-
  • SMILES C1=C(C(=CC2=NNC=C12)[N+](=O)[O-])Br

Description

5-Bromo-6-nitro-1H-indazole features a fused bicyclic core bearing a bromine atom at the 5-position and a nitro group at the 6-position, creating a highly electron-deficient heterocycle. This combination enables direct functionalization in cross-coupling reactions and enhances reactivity in transition-metal-catalyzed transformations. The molecule exhibits bench-stable handling characteristics and compatibility with standard synthetic protocols.

Application

5-Bromo-6-nitro-1H-indazole serves as a versatile building block for the synthesis of functionalized heterocycles and pharmaceutical intermediates. The bromo group enables palladium-catalyzed cross-coupling reactions, while the nitro group provides a handle for selective reduction and further derivatization. Its stability under standard reaction conditions and compatibility with diverse functional groups make it suitable for multi-step synthetic sequences in medicinal chemistry and process development.

Synthesis

  • Route1

    References

    • Zhu, Gui-Dong; Gong, Jianchun; Gandhi, Viraj B.; Woods, Keith; Luo, Yan; Liu, Xuesong; Guan, Ran; Klinghofer, Vered; Johnson, Eric F.; Stoll, Vincent S.; Mamo, Mulugeta; Li, Qun; Rosenberg, Saul H.; Giranda, Vincent L. Bioorganic and Medicinal Chemistry, 2007 , vol. 15, # 6 p. 2441 - 2452

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   71.82
  • LogP   2.2336
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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