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CS-W001157 4
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2-(1H-Imidazol-1-yl)aniline

  • CAS No. 26286-54-4

  • Cat. No. CS-0038189
  • Purity≥98%
  • MDL No.MFCD03274531

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

2-(1H-Imidazol-1-yl)aniline|CS-0038189

Structure of 26286-54-4

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General Information

  • CAS No. 26286-54-4
  • Cat. No. CS-0038189
  • Purity ≥98%
  • MDL No. MFCD03274531
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₉N₃
  • Molecular Weight 159.19
  • Synonym(s) Imidazole, 1-(o-aminophenyl)- (8CI)
  • SMILES C1=CC(=C(C=C1)N2C=CN=C2)N

Description

2-(1H-Imidazol-1-yl)aniline integrates a planar imidazole ring with an aniline scaffold, enabling strong π-stacking and hydrogen bonding. This dual functionality enhances coordination in metal complexes and facilitates supramolecular assembly. The molecule exhibits bench-stable behavior under standard conditions, offering reliable performance in catalytic and materials applications.

Application

2-(1H-Imidazol-1-yl)aniline serves as a versatile building block in medicinal chemistry, enabling the construction of bioactive heterocycles through its dual functional groups. The imidazole moiety offers strong hydrogen-bonding capacity and metabolic stability, while the aniline nitrogen facilitates coupling reactions and derivatization. This compound demonstrates excellent bench stability and compatibility with standard synthetic protocols, making it a reliable scaffold for developing kinase inhibitors and other pharmaceutical candidates.

Synthesis

  • Route1

    References

    • Wu, Feng-Tian; Liu, Ping; Ma, Xiao-Wei; Xie, Jian-Wei; Dai, Bin Chinese Chemical Letters, 2013 , vol. 24, # 10 p. 893 - 896
  • Route2

    References

    • Jansen, Eveline; Jongbloed, Linda S.; Tromp, Dorette S.; Lutz, Martin; De Bruin, Bas; Elsevier, Cornelis J. ChemSusChem, 2013 , vol. 6, # 9 p. 1737 - 1744
  • Route3
    • Imidazole Ondansetron Impurity|CS-0229601
      288-32-4
    • null|null
      615-36-1
    • ~85%
    • In-stock
      2-(1H-Imidazol-1-yl)aniline|CS-0038189
      26286-54-4

    References

    • Cross, Warren B.; Daly, Christopher G.; Boutadla, Youcef; Singh, Kuldip Dalton Transactions, 2011 , vol. 40, # 38 p. 9722 - 9730

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   43.84
  • LogP   1.4545
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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