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

  • CAS No. 152626-75-0

  • Cat. No. CS-0044776
  • Molecule weight193.16
  • Purity≥97%
  • MDL No.MFCD11007881

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

6-Methoxy-5-nitro-1H-indazole|CS-0044776

Structure of 152626-75-0

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General Information

  • CAS No. 152626-75-0
  • Cat. No. CS-0044776
  • Purity ≥97%
  • MDL No. MFCD11007881
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₇N₃O₃
  • Molecular Weight 193.16
  • Synonym(s) 6-Methoxy-5-nitroindazole
  • SMILES O=[N+](C1=CC2=C(NN=C2)C=C1OC)[O-]

Description

6-Methoxy-5-nitro-1H-indazole is a nitrogen-rich heterocycle featuring a methoxy group at the 6-position and a nitro substituent at the 5-position, conferring enhanced electron-withdrawing character. This combination enables efficient integration into bioactive scaffolds, particularly in medicinal chemistry leads requiring moderate lipophilicity and metabolic stability under standard conditions.

Application

6-Methoxy-5-nitro-1H-indazole serves as a versatile heterocyclic building block in medicinal chemistry, enabling efficient functionalization at the C6 position via cross-coupling reactions. The methoxy group provides synthetic handle for further derivatization, while the nitro functionality offers high reactivity in reduction and substitution processes. Bench-stable and compatible with standard purification methods, it facilitates rapid access to diverse indazole-based scaffolds relevant to API development.

Synthesis

  • Route1
    • N-(5-methoxy-2-methyl-4-nitrophenyl)acetamide|CS-0327561
      361162-90-5
    • ~%
    • In-stock
      6-Methoxy-5-nitro-1H-indazole|CS-0044776
      152626-75-0

    References

    • US2012/15962 A1, ; Page/Page column 89-90 ; US 20120015962 A1
  • Route2

    References

    • Bioorganic and Medicinal Chemistry, , vol. 12, # 9 p. 2115 - 2137
  • Route3

    References

    • Bioorganic and Medicinal Chemistry, , vol. 12, # 9 p. 2115 - 2137

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   81.05
  • LogP   1.4797
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   2

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