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CS-W001157 4
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Methyl 4-amino-2-methoxybenzoate

  • CAS No. 27492-84-8

  • Cat. No. CS-M2604
  • Purity≥98%
  • MDL No.MFCD00017202

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

Methyl 4-amino-2-methoxybenzoate|CS-M2604

Structure of 27492-84-8

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General Information

  • CAS No. 27492-84-8
  • Cat. No. CS-M2604
  • Purity ≥98%
  • MDL No. MFCD00017202
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₁₁NO₃
  • Molecular Weight 181.19
  • Synonym(s) Methyl 4-Amino-o-anisate
  • SMILES O=C(OC)C1=CC=C(N)C=C1OC

Description

Methyl 4-amino-2-methoxybenzoate features a para-amino group and ortho-methoxy substitution on the aromatic ring, delivering enhanced solubility and stability in polar solvents. This electron-rich scaffold integrates readily into synthetic routes for pharmaceutical intermediates and functional dyes, offering predictable reactivity under standard conditions.

Application

Methyl 4-amino-2-methoxybenzoate serves as a versatile synthetic intermediate in medicinal chemistry, enabling straightforward access to substituted anilines and heterocyclic scaffolds. Its ortho-methoxy group provides enhanced stability and facilitates selective functionalization, while the methyl ester offers a reliable handle for derivatization. The compound exhibits excellent bench stability and compatibility with standard coupling and reduction protocols, supporting efficient downstream transformations in API development workflows.

Synthesis

  • Route1

    References

    • Clinton et al. Journal of the American Chemical Society, 1952 , vol. 74, p. 592,595
  • Route2
    • 4-Aminosalicylic acid Mesalazine  Impurity|CS-0229166
      65-49-6
    • null|null
      77-78-1
    • ~72%
    • In-stock
      Methyl 4-amino-2-methoxybenzoate|CS-M2604
      27492-84-8

    References

    • Chiron, Julien; Galy, Jean-Pierre Heterocycles, 2003 , vol. 60, # 7 p. 1653 - 1672
  • Route3
    • In-stock
      Methyl 2-methoxy-4-nitrobenzoate|CS-0438987
      39106-79-1
    • null|null
      7440-05-3
    • ~85%
    • In-stock
      Methyl 4-amino-2-methoxybenzoate|CS-M2604
      27492-84-8

    References

    • American Cyanamid Company Patent: US5753648 A1, 1998 ; US 5753648 A

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-P330-P362-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   61.55
  • LogP   1.064
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   2

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