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CS-W001157 4
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4-Amino-2-methoxybenzoic acid

  • CAS No. 2486-80-8

  • Cat. No. CS-0150538
  • Molecule weight167.16
  • Purity≥98%
  • MDL No.MFCD00114479

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

4-Amino-2-methoxybenzoic acid|CS-0150538

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General Information

  • CAS No. 2486-80-8
  • Cat. No. CS-0150538
  • Purity ≥98%
  • MDL No. MFCD00114479
  • Storage RT, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₉NO₃
  • Molecular Weight 167.16
  • Synonym(s) m-Anisidine-4-carboxylic Acid
  • SMILES COC1=C(C=CC(=C1)N)C(=O)O

Description

4-Amino-2-methoxybenzoic acid features a strategically positioned amino group and methoxy substituent on the aromatic ring, enabling enhanced solubility and directional reactivity. This combination supports efficient coupling in peptide synthesis and conjugation workflows, particularly where electron-donating effects and hydrogen bonding capacity are advantageous.

Application

4-Amino-2-methoxybenzoic acid serves as a versatile building block in medicinal chemistry, enabling direct incorporation into diverse heterocyclic scaffolds and peptide conjugates. Its ortho-methoxy and para-amino groups provide orthogonal reactivity for selective derivatization, while the carboxylic acid facilitates amide coupling or esterification under standard conditions. The compound exhibits good bench stability and is readily purified by recrystallization, supporting scalable synthesis and integration into multi-step routes.

Synthesis

  • Route1

    References

    • Chakravarty, Sarvajit; Dugar, Sundeep; Lu, Qing; Luedtke, Gregory R.; Mavunkel, Babu J.; Perumattam, John J.; Tester, Richland W. Patent: US2004/142940 A1, 2004 ; Location in patent: Page/Page column 69-70 ; US 20040142940 A1
  • Route2

    References

    • Hewlett, William A.; De Paulis, Tomas; Mason, N. Scott; Schmidt, Dennis E.; Trivedi, Bakula L.; Zhang, Zhang-Jin; Ebert, Michael H. Chemical and Pharmaceutical Bulletin, 1997 , vol. 45, # 12 p. 2079 - 2084
  • Route3
    • Methyl 4-acetamido-2-methoxybenzoate Metoclopramide Impurity|CS-0229641
      4093-29-2
    • ~87%
    • In-stock
      4-Amino-2-methoxybenzoic acid|CS-0150538
      2486-80-8

    References

    • Barraclough, P.; Beams, R. M.; Black, J. W.; Cambridge, D.; Collard, D.; et al. European Journal of Medicinal Chemistry, 1990 , vol. 25, # 6 p. 467 - 477

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   72.55
  • LogP   0.9756
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   2

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