For chemists and chemical engineers involved in organic synthesis and process development, a thorough understanding of chemical intermediates is essential. 2-Amino-5-methoxybenzoic acid (CAS 6705-03-9) is one such compound, prized for its utility in creating complex organic molecules, particularly in the pharmaceutical and agrochemical sectors. This article explores its synthesis and key chemical properties.

Synthesis Pathways for 2-Amino-5-methoxybenzoic Acid

The preparation of 2-Amino-5-methoxybenzoic acid typically starts from readily available precursors. A common and efficient route involves the reduction of 5-methoxy-2-nitrobenzoic acid. This reduction is often achieved through catalytic hydrogenation using hydrogen gas (H2) in the presence of a palladium-on-carbon (Pd/C) catalyst. This method is known for yielding quantitative results, making it attractive for industrial-scale production by a chemical manufacturer.

Following the reduction of the nitro group to an amine, further derivatization can occur, such as forming disulfide compounds or amides, depending on the desired downstream products. For those interested in the specific chemical transformations and optimizing yields, detailed synthetic procedures are available, often referenced in patents and scientific literature. Understanding these processes is key for any organic synthesis professional looking to purchase or synthesize this compound.

Key Chemical Properties and Reactivity

2-Amino-5-methoxybenzoic acid is a bifunctional molecule, possessing both an amine group and a carboxylic acid group, in addition to a methoxy substituent on the aromatic ring. These functional groups dictate its chemical behavior and applications:

  • Amine Group: The primary amine can undergo reactions such as diazotization, acylation, and alkylation, making it a versatile starting point for amine-containing heterocycles.
  • Carboxylic Acid Group: This group can be esterified, converted into acid halides, or undergo decarboxylation under specific conditions. It also provides acidity to the molecule.
  • Aromatic Ring: The presence of the electron-donating methoxy and amino groups activates the aromatic ring for electrophilic aromatic substitution reactions, though careful control of reaction conditions is necessary due to the multiple activating substituents.
  • Physical Properties: Typically, it appears as a white to yellow to pale orange crystalline powder, with a melting point in the range of 148-152°C. Its solubility varies, being slightly soluble in methanol and other polar organic solvents.

These properties make it a sought-after intermediate for synthesizing complex molecules like Alogliptin and various heterocyclic compounds used in medicinal chemistry. Researchers frequently search for 2-Amino-5-methoxybenzoic acid synthesis routes to understand its production or to replicate it.

Sourcing Considerations

When procuring 2-Amino-5-methoxybenzoic acid for research or production, it is vital to consider its source. Working with a reliable fine chemical supplier like NINGBO INNO PHARMCHEM CO.,LTD. ensures access to a high-purity product with well-documented synthesis routes and consistent quality. We offer competitive pricing and technical support for professionals looking to purchase 2-amino-5-methoxybenzoic acid.

For detailed specifications, safety data, or to request a quote for bulk quantities of 2-Amino-5-methoxybenzoic acid, please contact NINGBO INNO PHARMCHEM CO.,LTD. We are committed to supporting your chemical synthesis endeavors.