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2-(2-Aminophenyl)acetic acid

  • CAS No. 3342-78-7

  • Cat. No. CS-0499254
  • Purity≥95%
  • MDL No.MFCD03701521

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

2-(2-Aminophenyl)acetic acid|CS-0499254

Structure of 3342-78-7

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General Information

  • CAS No. 3342-78-7
  • Cat. No. CS-0499254
  • Purity ≥95%
  • MDL No. MFCD03701521
  • Storage RT, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₉NO₂
  • Molecular Weight 151.16
  • Synonym(s) 2-Aminophenylacetic acid
  • SMILES NC1=CC=CC=C1CC(O)=O

Description

2-(2-Aminophenyl)acetic acid features a benzene ring bearing both amino and carboxylic acid functionalities in ortho proximity, enabling direct coordination to metal centers or integration into bioconjugation workflows. The pendant acetic acid group provides a handle for derivatization under standard coupling conditions, while the aromatic amine supports electrophilic substitution reactions. This scaffold exhibits enhanced solubility in polar solvents and maintains stability under ambient storage conditions.

Application

2-(2-Aminophenyl)acetic acid serves as a versatile building block for synthesizing bioactive heterocycles and pharmaceutical intermediates. Its ortho-aminobenzoic acid scaffold enables efficient cyclization reactions, including intramolecular amide formation and electrophilic substitution. The molecule exhibits good bench stability, facilitates straightforward purification via crystallization or chromatography, and tolerates common functional groups under standard coupling conditions, making it well-suited for medicinal chemistry and process development workflows.

Synthesis

  • Route1

    References

    • WO2012/28100 A1, ; Page/Page column 27 ; WO 2012/028100 A1
  • Route2
    • 2'-Aminoacetophenone Linagliptin Impurity|CS-0229112
      551-93-9
    • ~%
    • In-stock
      2-(2-Aminophenyl)acetic acid|CS-0499254
      3342-78-7

    References

    • Synthetic Communications, , vol. 33, # 1 p. 59 - 63
  • Route3

    References

    • Journal of the American Chemical Society, , vol. 58, p. 2241

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-H319
Precautionary Statements : P264-P270-P280-P330-P501

Quality Control

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Computational Chemistry Data

  • TPSA   63.32
  • LogP   0.8959
  • H_Acceptors   2
  • H_Donors   2
  • Rotatable_Bonds   2

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