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CS-W001157 4
Total: USD 88.00

5-Nitro-1H-indazole

  • CAS No. 5401-94-5

  • Cat. No. CS-B1273
  • Purity≥98%
  • MDL No.MFCD00005693

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

5-Nitro-1H-indazole|CS-B1273

Structure of 5401-94-5

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General Information

  • CAS No. 5401-94-5
  • Cat. No. CS-B1273
  • Purity ≥98%
  • MDL No. MFCD00005693
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₅N₃O₂
  • Molecular Weight 163.13
  • Synonym(s) 5-Nitroindazoles
  • SMILES O=[N+](C1=CC2=C(NN=C2)C=C1)[O-]

Description

5-Nitro-1H-indazole is a heterocyclic compound featuring a nitro group at the 5-position of the indazole scaffold. This electron-deficient moiety enhances reactivity in cross-coupling and cycloaddition processes. The molecule exhibits bench-stable handling characteristics and integrates readily into medicinal chemistry libraries.

Application

5-Nitro-1H-indazole serves as a versatile building block in medicinal chemistry, enabling direct functionalization at the C5 position via nitro group reduction or substitution. Its stability under standard reaction conditions and compatibility with common coupling protocols facilitate integration into complex heterocyclic scaffolds. The nitro group enhances electrophilicity for nucleophilic displacement, while the indazole core provides a rigid, bioisosteric platform for drug discovery applications.

Synthesis

  • Route1
    • null|null
      99-52-5
    • ~92%
    • In-stock
      5-Nitro-1H-indazole|CS-B1273
      5401-94-5

    References

    • Kym, Philip R.; Souers, Andrew J.; Campbell, Thomas J.; Lynch, John K.; Judd, Andrew S.; Iyengar, Rajesh; Vasudevan, Anil; Gao, Ju; Freeman, Jennifer C.; Wodka, Dariusz; Mulhern, Mathew; Zhao, Gang; Wagaw, Seble H.; Napier, James J.; Brodjian, Sevan; Dayton, Brian D.; Reilly, Regina M.; Segreti, Jason A.; Fryer, Ryan M.; Preusser, Lee C.; Reinhart, Glenn A.; Hernandez, Lisa; Marsh, Kennan C.; Sham, Hing L.; Collins, Christine A.; Polakowski, James S. Journal of Medicinal Chemistry, 2006 , vol. 49, # 7 p. 2339 - 2352
  • Route2

    References

    • Dandepally, Srinivasa Reddy; Williams, Alfred L. Tetrahedron Letters, 2009 , vol. 50, # 9 p. 1071 - 1074
  • Route3

    References

    • Wheeler, Rob C.; Baxter, Emma; Campbell, Ian B.; MacDonald, Simon J. F. Organic Process Research and Development, 2011 , vol. 15, # 3 p. 565 - 569

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   1.4711
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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