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2-(1H-Imidazol-1-yl)benzoic acid

  • CAS No. 159589-67-0

  • Cat. No. CS-0096794
  • Molecule weight188.19
  • Purity≥98%
  • MDL No.MFCD06254507

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

2-(1H-Imidazol-1-yl)benzoic acid|CS-0096794

Structure of 159589-67-0

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General Information

  • CAS No. 159589-67-0
  • Cat. No. CS-0096794
  • Purity ≥98%
  • MDL No. MFCD06254507
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₈N₂O₂
  • Molecular Weight 188.19
  • Synonym(s) 2-Imidazol-1-ylbenzoic acid
  • SMILES O=C(O)C=1C=CC=CC1N2C=NC=C2

Description

This imidazolylbenzoic acid integrates a bioactive imidazole moiety with a carboxylic acid handle, enabling direct conjugation in medicinal chemistry. The ortho-arranged heterocycle enhances rigidity and target engagement potential, while the acidic function supports salt formation and solubility modulation under standard conditions.

Application

2-(1H-Imidazol-1-yl)benzoic acid serves as a versatile building block in medicinal chemistry, enabling the construction of biologically relevant heterocyclic scaffolds. Its imidazole moiety offers enhanced solubility and hydrogen-bonding capacity, while the carboxylic acid group facilitates direct conjugation or derivatization in standard coupling reactions. The molecule exhibits good bench stability and is compatible with diverse functional groups, making it well-suited for parallel synthesis campaigns and API intermediate development.

Synthesis

  • Route1

    References

    • Sreedhar; Arundhathi; Linga Reddy; Amarnath Reddy; Lakshmi Kantam Synthesis, 2009 , # 15 art. no. P03909SS, p. 2517 - 2522
  • Route2

    References

    • Li, Xufeng; Yang, Daoshan; Jiang, Yuyang; Fu, Hua Green Chemistry, 2010 , vol. 12, # 6 p. 1097 - 1105
  • Route3
    • 2-(1H-Imidazol-1-yl)benzonitrile|CS-0206631
      25373-49-3
    • ~%
    • In-stock
      2-(1H-Imidazol-1-yl)benzoic acid|CS-0096794
      159589-67-0

    References

    • Chemical and Pharmaceutical Bulletin, , vol. 53, # 7 p. 764 - 769

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : 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   55.12
  • LogP   1.5705
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   2

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