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CS-W001157 4
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3-Carbamoylbenzoic acid

  • CAS No. 4481-28-1

  • Cat. No. CS-0149777
  • Purity≥97%
  • MDL No.MFCD04118098

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

3-Carbamoylbenzoic acid|CS-0149777

Structure of 4481-28-1

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General Information

  • CAS No. 4481-28-1
  • Cat. No. CS-0149777
  • Purity ≥97%
  • MDL No. MFCD04118098
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₇NO₃
  • Molecular Weight 165.15
  • Synonym(s) 3-CARBOXAMIDOBENZOIC ACID
  • SMILES O=C(O)C1=CC=CC(C(N)=O)=C1

Description

3-Carbamoylbenzoic acid features a carboxylic acid group ortho to a carbamoyl substituent, enabling direct integration into peptide mimetics and bioactive scaffolds. This polar, bench-stable motif facilitates hydrogen bonding in target binding interfaces and enhances solubility in aqueous-organic mixtures.

Application

3-Carbamoylbenzoic acid serves as a versatile building block in medicinal chemistry, enabling the construction of bioactive heterocycles and peptide-like scaffolds. Its dual carboxylic acid and amide functionalities offer orthogonal reactivity for coupling reactions, amidation, and cyclization processes. The molecule exhibits good bench stability and facilitates straightforward purification via recrystallization or chromatography, making it well-suited for iterative synthesis workflows in API development.

Synthesis

  • Route1

    References

    • Constantino, Luis; Iley, Jim Xenobiotica, 1999 , vol. 29, # 4 p. 409 - 416
  • Route2
    • Methyl 3-(benzylcarbamoyl)benzoate|CS-0205607
      925159-45-1
    • ~44%
    • In-stock
      3-Carbamoylbenzoic acid|CS-0149777
      4481-28-1
    • In-stock
      Methyl 3-carbamoylbenzoate|CS-0150664
      106748-24-7

    References

    • Rombouts, Frederik; Franken, Dennis; Martinez-Lamenca, Carolina; Braeken, Mirielle; Zavattaro, Chiara; Chen, Jinsheng; Trabanco, Andres A. Tetrahedron Letters, 2010 , vol. 51, # 37 p. 4815 - 4818
  • Route3

    References

    • I.G. Farbendind. Patent: DE745447 , 1940 ; DRP/DRBP Org.Chem.

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H315-H319-H335
Precautionary Statements : P261-P264-P271-P280-P302+P352

Quality Control

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Computational Chemistry Data

  • TPSA   80.39
  • LogP   0.4837
  • H_Acceptors   2
  • H_Donors   2
  • Rotatable_Bonds   2

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