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CS-W001157 4
Total: USD 88.00

6-Nitro-1H-benzo[d]imidazol-2-amine

  • CAS No. 6232-92-4

  • Cat. No. CS-D1074
  • Purity≥97%
  • MDL No.MFCD06659794

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

6-Nitro-1H-benzo[d]imidazol-2-amine|CS-D1074

Structure of 6232-92-4

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General Information

  • CAS No. 6232-92-4
  • Cat. No. CS-D1074
  • Purity ≥97%
  • MDL No. MFCD06659794
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₆N₄O₂
  • Molecular Weight 178.15
  • Synonym(s) 2-Amino-6-nitrobenzimidazole
  • SMILES NC1=NC2=CC=C([N+]([O-])=O)C=C2N1

Description

6-Nitro-1H-benzo[d]imidazol-2-amine features a fused bicyclic core with a nitro group at the 6-position and an amino substituent at the 2-position, delivering enhanced electron deficiency and reactivity. This configuration enables efficient coupling in synthetic transformations and facilitates incorporation into bioactive scaffolds. The compound exhibits bench-stable handling characteristics and compatibility with diverse reaction conditions.

Application

6-Nitro-1H-benzo[d]imidazol-2-amine serves as a versatile building block in heterocyclic synthesis, enabling efficient access to bioactive scaffolds through selective functionalization at the amine and nitro positions. Its stability under standard reaction conditions facilitates downstream transformations, including reduction, coupling, and cyclization, making it valuable for medicinal chemistry and materials development.

Synthesis

  • Route1
    • null|null
      506-68-3
    • null|null
      99-56-9
    • ~98%
    • In-stock
      6-Nitro-1H-benzo[d]imidazol-2-amine|CS-D1074
      6232-92-4

    References

    • Huigens III, Robert W.; Reyes, Samuel; Reed, Catherine S.; Bunders, Cynthia; Rogers, Steven A.; Steinhauer, Andrew T.; Melander, Christian Bioorganic and Medicinal Chemistry, 2010 , vol. 18, # 2 p. 663 - 674
  • Route2
    • In-stock
      Amino(imino)methanesulfonic acid|CS-0134092
      1184-90-3
    • null|null
      99-56-9
    • ~89%
    • In-stock
      6-Nitro-1H-benzo[d]imidazol-2-amine|CS-D1074
      6232-92-4

    References

    • Mohanazadeh, Farajollah; Nami, Navabe; Hosseini, Samine Sadat Chinese Journal of Chemistry, 2011 , vol. 29, # 5 p. 1055 - 1058
  • Route3
    • null|null
      75966-22-2
    • ~54%
    • In-stock
      6-Nitro-1H-benzo[d]imidazol-2-amine|CS-D1074
      6232-92-4
    • null|null
      70297-92-6

    References

    • Schulze, Juergen; Tanneberg, Hartmut; Matschiner, Hermann Zeitschrift fuer Chemie (Stuttgart, Germany), 1980 , vol. 20, # 12 p. 436 - 437

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-H319
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   97.84
  • LogP   1.0533
  • H_Acceptors   4
  • H_Donors   2
  • Rotatable_Bonds   1

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