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CS-W001157 4
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2-Oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylic acid

  • CAS No. 23814-14-4

  • Cat. No. CS-W005273
  • Purity≥98%
  • MDL No.MFCD01233165

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

2-Oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylic acid|CS-W005273

Structure of 23814-14-4

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General Information

  • CAS No. 23814-14-4
  • Cat. No. CS-W005273
  • Purity ≥98%
  • MDL No. MFCD01233165
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₆N₂O₃
  • Molecular Weight 178.15
  • Synonym(s) 2-OXO-2,3-DIHYDRO-1H-BENZOIMIDAZOLE-5-CARBOXYLIC ACID
  • SMILES O=C(C1=CC=C(C(N2)=C1)NC2=O)O

Description

This benzoimidazole derivative features a carboxylic acid group at the 5-position, enhancing solubility and reactivity in synthetic transformations. The oxo functionality at C2 imparts electrophilic character, enabling use in heterocyclic coupling reactions. Bench-stable and moisture-tolerant, it serves as a valuable scaffold for medicinal chemistry and materials science applications.

Application

2-Oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylic acid serves as a versatile heterocyclic building block for medicinal chemistry and materials science applications. Its fused benzimidazole core provides structural rigidity and hydrogen-bonding capability, while the carboxylic acid and oxo functionalities enable facile derivatization via amide formation, esterification, or metal-catalyzed coupling reactions. The compound exhibits good bench stability and is compatible with standard purification techniques, facilitating integration into multi-step synthetic sequences.

Synthesis

  • Route1
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    • In-stock
      4-Carboxyphenyldiamine|CS-D1364
      619-05-6
    • ~%
    • In-stock
      2-Oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylic acid|CS-W005273
      23814-14-4

    References

    • Dombroski, Mark A.; Letavic, Michael A.; McClure, Kim F.; Barberia, John T.; Carty, Thomas J.; Cortina, Santo R.; Csiki, Csilla; Dipesa, Alan J.; Elliott, Nancy C.; Gabel, Christopher A.; Jordan, Crystal K.; Labasi, Jeff M.; Martin, William H.; Peese, Kevin M.; Stock, Ingrid A.; Svensson, Linne; Sweeney, Francis J.; Yu, Chul H. Bioorganic and Medicinal Chemistry Letters, 2004 , vol. 14, # 4 p. 919 - 923
  • Route2
    • 3-(Carbamoylamino)benzoic acid|CS-0037838
      20632-43-3
    • ~%
    • In-stock
      2-Oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylic acid|CS-W005273
      23814-14-4

    References

    • Griess Chemische Berichte, 1872 , vol. 5, p. 201 Journal fuer Praktische Chemie (Leipzig), 1872 , vol. <2> 5, p. 241

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   85.95
  • LogP   0.5544
  • H_Acceptors   2
  • H_Donors   3
  • Rotatable_Bonds   1

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