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Understanding CAS No: 2374-03-0 — 4-Amino-3-Hydroxybenzoic Acid

In the world of organic chemistry, certain compounds quietly play indispensable roles in scientific research and industrial applications. One such compound is 4-Amino-3-hydroxybenzoic acid, identified by its unique CAS number 2374-03-0. Though it may not be a household name, this chemical’s distinctive structure and multifaceted utility make it significant in pharmaceuticals, materials science, and chemical synthesis.

Chemical Identity and Structure

4-Amino-3-hydroxybenzoic acid is an aromatic compound with the molecular formula C₇H₇NO₃ and a molecular weight of 153.14 g/mol. Its structure includes three key functional groups attached to a benzene ring:

an amino group (-NH₂) at the 4-position,

a hydroxyl group (-OH) at the 3-position, and

a carboxylic acid group (-COOH).

This arrangement of substituents imparts unique chemical behavior. The amino and hydroxyl groups are electron-donating, while the carboxyl group is electron-withdrawing — a combination that influences reactivity, acidity, and interactions with other molecules.

Physically, the compound typically appears as a yellow-brown to brown crystalline powder. It has a melting point of about 211–215 °C and a high boiling point (~385 °C), underscoring its robust thermal stability compared with many small organic molecules.

Chemical Properties and Behavior

From a chemical perspective, the presence of both the –NH₂ and –OH groups enhances its hydrogen-bonding capabilities, making the compound reactive in both acid-base chemistry and nucleophilic substitution reactions. The compound is partially soluble in water, but shows greater solubility in organic solvents like chloroform, methanol, and ethanol. These solubility traits are important considerations for lab handling and formulation. 

Due to its mixed functionality, 4-Amino-3-hydroxybenzoic acid can participate in many types of reactions typical of aromatic compounds:

Acylation and esterification involving the carboxyl group

Diazonium coupling due to the amine

Oxidation and reduction reactions involving the hydroxyl group

These characteristics make it a versatile building block in organic synthesis.

Applications in Pharmaceutical Chemistry

One of the most prominent areas where this compound finds use is pharmaceutical synthesis. It is frequently employed as an intermediate in the creation of more complex drug molecules. Its functional groups can be elaborated into diverse chemical frameworks that form the backbone of biologically active compounds. 

Specifically, derivatives of 4-Amino-3-hydroxybenzoic acid are used in the preparation of sphingosine kinase inhibitors, which are studied for potential roles in treating cancer and inflammatory diseases. By serving as a precursor that can be chemically manipulated, the compound contributes to medicinal chemistry programs focused on targeted disease therapies. 

Beyond inhibitors, its scaffold has been adaptable in synthesizing other therapeutic agents where aromatic substitution patterns are crucial for biological activity.

Organic Synthesis and Material Science

Outside pharmaceuticals, this benzoic acid derivative is also valued in organic synthesis more broadly. In research settings, it serves as a precursor for heterocyclic compounds and other functional materials. For example, some studies explore its incorporation into polymer precursors for high-performance materials, taking advantage of its ability to undergo cyclization and ring-forming transformations.

Because the compound’s structure combines both reactivity and rigidity (from the benzene ring), it is also useful in materials chemistry where stable yet modifiable aromatic intermediates are required.

Safety and Handling

Like many laboratory chemicals, 4-Amino-3-hydroxybenzoic acid must be handled with respect for safety. It is generally classified as an irritant — capable of causing irritation to the skin, eyes, and respiratory system. Ingestion may also be harmful. 

Standard laboratory safety practices should be observed when working with this compound:

Wear appropriate protective equipment (gloves, eye protection).

Work in a well-ventilated area or under a fume hood.

Avoid inhalation of dust or prolonged skin contact.

In case of exposure, rinse thoroughly and seek medical advice if necessary.

Conclusion

Cas No: 2374-03-0 | 4-Amino-3-Hydroxy Benzoic Acid

Exploring 4-Amino-3-HydroxyBenzoic Acid (CAS No: 2374-03-0): A Key Compound in Chemistry and Medicine

In the realm of organic chemistry, compounds with a unique combination of functional groups can exhibit remarkable properties. One such compound is 4-Amino-3-HydroxyBenzoic Acid, identified by its Chemical Abstracts Service (CAS) number 2374-03-0. This compound plays a significant role in various scientific and industrial applications, ranging from the development of pharmaceutical agents to its potential use in research and manufacturing.

What is 4-Amino-3-HydroxyBenzoic Acid?

4-Amino-3-Hydroxy Benzoic Acid is an organic compound that belongs to the family of benzoic acids. Its structure consists of a benzene ring, with two key substituents:

Amino group (-NH2) attached at the 4-position.

Hydroxyl group (-OH) attached at the 3-position.

This arrangement makes it a derivative of salicylic acid, which is the base compound for many aspirin-like drugs. However, the introduction of the amino group opens up new avenues for chemical reactions and biological interactions.

Chemical Structure and Properties

The IUPAC name for 4-Amino-3-HydroxyBenzoic Acid is 3-hydroxy-4-aminobenzoic acid, reflecting the locations of the functional groups on the benzene ring. With the molecular formula C7H7NO3, the compound is a white to off-white solid, typically in crystalline form. The key physical properties include:

Molecular weight: 167.14 g/mol

Melting point: Around 180–185°C

Solubility: It is sparingly soluble in water but soluble in organic solvents such as ethanol and methanol.

The hydroxyl group (–OH) and the amino group (–NH2) contribute to its potential reactivity, allowing it to be involved in diverse reactions such as esterification, nucleophilic substitution, and condensation.

Applications in Pharmaceutical and Medicinal Chemistry

4-Amino-3-Hydroxy Benzoic Acid is primarily known for its role in the development of drugs and pharmaceuticals. Its structural similarity to salicylic acid (the active ingredient in aspirin) makes it a valuable starting point for the synthesis of compounds with anti-inflammatory and analgesic properties. By modifying its structure, researchers can create derivatives with enhanced biological activity.

One of the most notable applications of 4-Amino-3-Hydroxy Benzoic Acid is its involvement in the synthesis of para-aminosalicylic acid (PAS). PAS has been historically used as an anti-tuberculosis drug, especially in the era before more modern antibiotics were developed. The compound is effective in combating the tuberculosis-causing bacteria Mycobacterium tuberculosis, and its derivatives continue to be studied for their potential in treating resistant strains.

In addition to its use in tuberculosis treatments, 4-Amino-3-Hydroxy Benzoic Acid is a key intermediate in the manufacture of azo dyes. These dyes are widely used in the textile industry and also find applications in biological staining techniques.

Research and Analytical Uses

Due to its structural characteristics, 4-Amino-3-Hydroxy Benzoic Acid is also useful in research settings. In particular, it is used as a pH indicator, as the pKa values of the amino and hydroxyl groups make it sensitive to changes in pH. Additionally, its chemical properties make it an ideal candidate for studying the interaction between organic compounds and biological systems.

Scientists and chemists have studied 4-Amino-3-HydroxyBenzoic Acid in relation to its ability to form complexes with metal ions. This property is valuable in fields such as coordination chemistry and environmental science, where it is used in the detection and removal of heavy metals from solutions.

Environmental Impact and Safety

As with many chemicals, it is essential to consider the environmental and safety implications of using 4-Amino-3-HydroxyBenzoic Acid. The compound is not typically regarded as highly toxic, but as with most chemical reagents, it should be handled with care. It is advisable to avoid inhalation or direct contact with the skin or eyes, as it can cause irritation. Moreover, as with many synthetic chemicals, appropriate disposal methods should be followed to prevent contamination of soil and water resources.

Conclusion

4-Amino-3-HydroxyBenzoic Acid (CAS No: 2374-03-0) is a fascinating compound with diverse applications in both medicinal chemistry and industrial processes. Whether in the development of anti-tuberculosis drugs, the creation of azo dyes, or its utility as a pH indicator in laboratory research, its unique structure and reactivity continue to make it an important compound in the world of chemistry.

For researchers, chemists, and pharmaceutical developers, understanding the properties and uses of compounds like 4-Amino-3-HydroxyBenzoic Acid can lead to innovations in medicine and industry, while also offering new pathways for scientific discovery.

Amino

No harm of hydroxy chloroquine, COVID-19 can be used for: ICMR

Studies in India did not reveal any major loss of hydroxychloroquine.

new Delhi:

The Indian Council of Medical Research (ICMR) said on Tuesday that studies in India have not revealed any major side effects of the anti-malarial drug hydroxychloroquine (HCQ) and that it may be continued under strict medical supervision in precautionary treatment of Kovid-19. Can. The ICMR’s statement comes at a…