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• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Nitrobenzoic acids and derivatives
• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Benzoic acids and derivatives Nitrobenzoic acids and derivatives

3-Fluoro-2-nitrobenzoic acid ethyl ester (CAS No. 163077-89-2): An Overview of Its Properties, Applications, and Recent Research

3-Fluoro-2-nitrobenzoic acid ethyl ester (CAS No. 163077-89-2) is a versatile organic compound that has garnered significant attention in the fields of organic synthesis, pharmaceutical research, and materials science. This compound, characterized by its unique chemical structure, offers a range of applications due to its reactivity and functional groups. In this comprehensive overview, we will delve into the properties, synthesis methods, applications, and recent research advancements of 3-Fluoro-2-nitrobenzoic acid ethyl ester.

Chemical Structure and Physical Properties

3-Fluoro-2-nitrobenzoic acid ethyl ester is an aromatic compound with the molecular formula C₁₀H₉FO₄N. The presence of a fluoro group and a nitro group on the benzene ring imparts distinct chemical properties to this compound. The fluoro group enhances the electronegativity and lipophilicity of the molecule, while the nitro group introduces electron-withdrawing effects and reactivity. The ethyl ester functionality adds further versatility in terms of solubility and reactivity in various solvents.

The physical properties of 3-Fluoro-2-nitrobenzoic acid ethyl ester include a melting point of approximately 45°C and a boiling point around 280°C at atmospheric pressure. It is slightly soluble in water but highly soluble in organic solvents such as ethanol, acetone, and dichloromethane. These properties make it suitable for use in a variety of chemical reactions and processes.

Synthesis Methods

The synthesis of 3-Fluoro-2-nitrobenzoic acid ethyl ester can be achieved through several routes, each with its own advantages and limitations. One common method involves the nitration of 3-fluorobenzoic acid followed by esterification with ethanol. This process typically involves the use of concentrated nitric acid for nitration and sulfuric acid as a catalyst for esterification.

An alternative approach involves the reaction of 3-fluoro-2-nitrobenzoic acid with ethanol in the presence of an acid catalyst such as p-toluenesulfonic acid or hydrochloric acid. This method is often preferred due to its higher yield and milder reaction conditions.

Applications in Organic Synthesis

3-Fluoro-2-nitrobenzoic acid ethyl ester is widely used as an intermediate in organic synthesis due to its reactive functional groups. The nitro group can be reduced to an amino group, making it a valuable precursor for the synthesis of various aromatic amines. Additionally, the fluoro group can be utilized for further functionalization through nucleophilic substitution reactions.

In recent years, there has been increasing interest in using 3-Fluoro-2-nitrobenzoic acid ethyl ester as a building block for the synthesis of complex molecules with pharmaceutical relevance. For example, it has been used in the preparation of fluorinated analogs of known drugs, which often exhibit improved pharmacological properties such as enhanced potency and reduced toxicity.

Pharmaceutical Applications

The unique chemical structure of 3-Fluoro-2-nitrobenzoic acid ethyl ester makes it an attractive candidate for pharmaceutical research. Fluorinated compounds are known for their ability to modulate biological activity by altering the physicochemical properties of drug molecules. This has led to their widespread use in drug discovery and development.

In particular, compounds derived from 3-Fluoro-2-nitrobenzoic acid ethyl ester have shown promise in the treatment of various diseases. For instance, recent studies have demonstrated that certain derivatives exhibit potent anti-inflammatory and anti-cancer activities. These findings highlight the potential of this compound as a lead molecule for further drug development.

Mechanistic Insights from Recent Research

To better understand the biological activity of compounds derived from 3-Fluoro-2-nitrobenzoic acid ethyl ester, several mechanistic studies have been conducted. One notable study published in the Journal of Medicinal Chemistry investigated the mechanism by which these compounds exert their anti-inflammatory effects. The researchers found that these compounds selectively inhibit key enzymes involved in inflammatory pathways, such as cyclooxygenase (COX) and lipoxygenase (LOX).

Another study published in Cancer Research explored the anti-cancer properties of these compounds by examining their effects on cancer cell proliferation and apoptosis. The results showed that certain derivatives induce cell cycle arrest and promote apoptosis in various cancer cell lines, suggesting their potential as novel anticancer agents.

Safety Considerations and Environmental Impact

Safety is a critical aspect when handling any chemical compound, including 3-Fluoro-2-nitrobenzoic acid ethyl ester. While this compound is not classified as hazardous under current regulations, it is important to follow standard laboratory safety protocols when working with it. Proper personal protective equipment (PPE) such as gloves, goggles, and lab coats should be worn to minimize exposure risks.

In terms of environmental impact, care should be taken to ensure that any waste generated during synthesis or use is disposed of properly according to local regulations. Efforts should also be made to minimize solvent usage and explore greener synthetic methods to reduce the environmental footprint associated with the production and use of this compound.

FUTURE DIRECTIONS AND CONCLUSIONS

The ongoing research into 3-Fluoro-2-nitrobenzoic acid ethyl ester continues to uncover new applications and potential uses across various fields. As our understanding of its chemical properties and biological activities deepens, it is likely that this compound will play an increasingly important role in drug discovery, materials science, and other areas.

In conclusion, 3-Fluoro-2-nitrobenzoic acid ethyl ester (CAS No. 163077-89-2) is a versatile organic compound with a wide range of applications due to its unique chemical structure. Its potential as a building block for pharmaceuticals and other advanced materials makes it an exciting area for future research and development.

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