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CS-W001157 4
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3-Amino-5-(methoxycarbonyl)benzoic acid

  • CAS No. 28179-47-7

  • Cat. No. CS-0046171
  • Purity≥98%
  • MDL No.MFCD00224870

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

3-Amino-5-(methoxycarbonyl)benzoic acid|CS-0046171

Structure of 28179-47-7

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General Information

  • CAS No. 28179-47-7
  • Cat. No. CS-0046171
  • Purity ≥98%
  • MDL No. MFCD00224870
  • Storage RT, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₉NO₄
  • Molecular Weight None
  • Synonym(s) Monomethyl 5-Aminoisophthalate
  • SMILES O=C(C1=CC(N)=CC(C(O)=O)=C1)OC

Description

3-Amino-5-(methoxycarbonyl)benzoic acid features a dual functional group array: an electron-rich amino moiety flanked by a methoxycarbonyl ester and a carboxylic acid. This combination enables direct incorporation into peptide couplings, bioconjugation strategies, and heterocyclic synthesis under standard conditions. The molecule exhibits favorable solubility in common organic solvents and stability during routine handling.

Application

3-Amino-5-(methoxycarbonyl)benzoic acid serves as a versatile building block in medicinal chemistry, enabling the synthesis of substituted benzimidazoles, quinazolines, and other heterocyclic scaffolds. The ortho-amino and ester-carboxylic acid functionalities offer complementary reactivity for coupling reactions, cyclizations, and derivatization under standard conditions. Its bench-stable crystalline form facilitates handling and purification, while the methoxycarbonyl group provides a reliable handle for selective hydrolysis or further functionalization.

Synthesis

  • Route1

    References

    • BRISTOL-MYERS SQUIBB COMPANY Patent: WO2009/15166 A1, 2009 ; Location in patent: Page/Page column 87 ; WO 2009/015166 A1

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   89.62
  • LogP   0.7536
  • H_Acceptors   4
  • H_Donors   2
  • Rotatable_Bonds   2

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