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CS-W001157 4
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2-(3-Nitrophenyl)imidazole

  • CAS No. 13682-18-3

  • Cat. No. CS-0156980
  • Molecule weight189.17
  • Purity≥98%
  • MDL No.MFCD05863370

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

2-(3-Nitrophenyl)imidazole|CS-0156980

Structure of 13682-18-3

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General Information

  • CAS No. 13682-18-3
  • Cat. No. CS-0156980
  • Purity ≥98%
  • MDL No. MFCD05863370
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₇N₃O₂
  • Molecular Weight 189.17
  • Synonym(s) 2-(3-NITRO-PHENYL)-1H-IMIDAZOLE
  • SMILES C1=CC(=CC(=C1)[N+](=O)[O-])C2=NC=CN2

Description

2-(3-Nitrophenyl)imidazole is a bench-stable heterocyclic compound featuring an electron-deficient imidazole core fused to a nitro-substituted phenyl ring. This structural combination enables direct integration into transition-metal-catalyzed coupling reactions, where the para-nitro group serves as a handle for further functionalization. The molecule exhibits enhanced solubility in polar organic solvents and demonstrates robust stability under standard handling conditions.

Application

2-(3-Nitrophenyl)imidazole serves as a versatile building block in medicinal chemistry, enabling the construction of biologically active heterocyclic scaffolds. Its ortho-nitroaryl group facilitates electrophilic substitution and transition-metal-catalyzed coupling reactions, while the imidazole core provides hydrogen-bonding capacity and metabolic stability. The compound exhibits bench stability and compatibility with standard purification methods, making it suitable for iterative synthesis workflows in API development.

Synthesis

  • Route1

    References

    • KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY; HAH, Jung-Mi; YOO, Kyung Ho; SIM, Tae-Bo; OH, Chang Hyun; LEE, Jung Hun; YU, Hana; KIM, Hwan Patent: WO2011/49274 A1, 2011 ; Location in patent: Page/Page column 17 ; WO 2011/049274 A1
  • Route2
    • null|null
      131543-46-9
    • 3-Nitrobenzaldehyde Erlotinib Impurity|CS-0204123
      99-61-6
    • ~%
    • In-stock
      2-(3-Nitrophenyl)imidazole|CS-0156980
      13682-18-3

    References

    • WO2006/17443 A2, ; Page/Page column 176-177 ; WO 2006/017443 A2
  • Route3
    • In-stock
      2,2-Dimethoxyethanamine|CS-0015304
      22483-09-6
    • null|null
      54316-43-7
    • ~%
    • In-stock
      2-(3-Nitrophenyl)imidazole|CS-0156980
      13682-18-3

    References

    • US6211220 B1, ;

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   71.82
  • LogP   1.9849
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   2

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