2-Amino-5-methoxybenzoic acid
[CAS# 6705-03-9]

Identification

• Classification: Biochemical >> Amino acids and their derivatives >> Other amino acid derivatives
• Name: 2-Amino-5-methoxybenzoic acid
• Molecular Formula: C₈H₉NO₃
• Molecular Weight: 167.16
• CAS Registry Number: 6705-03-9
• EC Number: 628-679-4
• SMILES: COC1=CC(=C(C=C1)N)C(=O)O

Properties

• Melting point: 148-152 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

2-Amino-5-methoxybenzoic acid is an organic compound belonging to the aminobenzoic acids family. Its discovery can be traced back to early 20th-century chemical research focusing on the synthesis and characterization of substituted benzoic acids. It was synthesized through the nitration and subsequent reduction of 5-methoxyaniline followed by carboxylation. The chemical structure of 2-amino-5-methoxybenzoic acid was confirmed using spectroscopic techniques such as nuclear magnetic resonance (NMR) and mass spectrometry (MS). This compound's unique structure, featuring both an amino group and a methoxy group on a benzoic acid core, makes it valuable for various applications in pharmaceuticals, chemical synthesis, and materials science.

2-Amino-5-methoxybenzoic acid is a crucial intermediate in the synthesis of various pharmaceuticals. Its unique structure allows for the creation of bioactive compounds that can target specific biological pathways. It is used to develop drugs with anti-inflammatory, analgesic, and antimicrobial properties. The amino and methoxy groups facilitate the formation of derivatives that enhance the compound's pharmacological activity and bioavailability.

In organic synthesis, 2-amino-5-methoxybenzoic acid is used as a building block for more complex molecules. It participates in various reactions such as coupling, substitution, and condensation, making it valuable for creating heterocyclic compounds, dyes, and agrochemicals. Its ability to introduce functional groups into molecules makes it a versatile reagent in synthetic chemistry.

The compound finds applications in materials science, particularly in the development of polymers and advanced materials. The presence of both amino and methoxy groups allows it to be incorporated into polymer backbones, enhancing properties such as thermal stability, mechanical strength, and chemical resistance. These polymers are used in coatings, adhesives, and other high-performance materials.

2-Amino-5-methoxybenzoic acid is used in academic and industrial research to study chemical reactions and develop new synthetic methodologies. Its multifunctional nature makes it an ideal candidate for exploring novel transformations and reaction mechanisms. Researchers utilize it to design new compounds with potential applications in various fields, driving innovation and expanding the frontiers of chemical science.

The compound is also significant in the agrochemical industry for synthesizing herbicides, fungicides, and plant growth regulators. Its structural attributes allow for the creation of effective active ingredients that protect crops from pests and diseases, thereby improving agricultural productivity and sustainability.

References

2020. Expedient Approach to the Synthesis of Betrixaban. SynOpen, 4.
DOI: 10.1055/s-0040-1707267

2016. Concise Synthesis of Dictyoquinazol A via a Dimerisation-Cyclocondensation Sequence. Synlett, 27(6).
DOI: 10.1055/s-0035-1561569

1972. Reaction of anthranilic acid and methoxy- and nitro-substituted anthranilic acid with p-toluenesulfonyl chloride in pyridine. Chemistry of Heterocyclic Compounds, 8(10).
DOI: 10.1007/bf00475532