5-Fluoro-2-(trifluoromethyl)benzenamine
[CAS# 827-20-3]

Identification

• Classification: Organic raw materials >> Organic fluorine compound >> Fluorotoluene series
• Name: 5-Fluoro-2-(trifluoromethyl)benzenamine
• Synonyms: a,a,a,5-Tetrafluoro-o-toluidine
• Molecular Formula: C₇H₅F₄N
• Molecular Weight: 179.11
• CAS Registry Number: 827-20-3
• EC Number: 679-061-6
• SMILES: C1=CC(=C(C=C1F)N)C(F)(F)F

Properties

• Density: 1.4±0.1 g/cm³ Calc.^*
• Melting point: 29 - 32 °C (Expl.)
• Boiling point: 185.6±35.0 °C 760 mmHg (Calc.)^*
• Flash point: 74.4±16.4 °C (Calc.)^*
• Index of refraction: 1.46 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS06 Danger
• Risk Statements: H302-H311-H315-H319-H332
• Safety Statements: P261-P262-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P316-P317-P321-P330-P332+P317-P337+P317-P361+P364-P362+P364-P405-P501

Discovery and Applications

5-Fluoro-2-(trifluoromethyl)benzenamine is an organic compound belonging to the class of aniline derivatives. Its structure consists of a benzene ring substituted with two functional groups: a fluorine atom at the 5-position and a trifluoromethyl group (-CF3) at the 2-position of the benzene ring. The molecular formula for 5-fluoro-2-(trifluoromethyl)benzenamine is C7H5F4N, and it features a trifluoromethyl group, a highly electronegative and bulky substituent, which imparts unique chemical and physical properties to the molecule.

This compound is typically synthesized by introducing the trifluoromethyl group and the fluorine atom into the benzene ring through various fluorination techniques. One of the common methods is through electrophilic aromatic substitution reactions, where the introduction of the trifluoromethyl group and fluorine is facilitated by the use of specialized reagents under controlled conditions. The resulting molecule can then undergo further modifications to yield a wide variety of derivatives, each with distinct properties.

5-Fluoro-2-(trifluoromethyl)benzenamine has found applications in several fields, including medicinal chemistry and materials science, owing to the unique properties imparted by the trifluoromethyl and fluorine groups. The presence of the trifluoromethyl group in particular is of significant interest due to its electron-withdrawing nature, which can influence the reactivity and polarity of the compound, making it a valuable intermediate in the synthesis of other organic compounds.

In medicinal chemistry, 5-fluoro-2-(trifluoromethyl)benzenamine and its derivatives have been explored for their potential biological activities. The trifluoromethyl group can enhance the metabolic stability and lipophilicity of organic molecules, which can improve their bioavailability and pharmacokinetic properties. Compounds with these structural features have been studied for their ability to interact with various biological targets, including receptors and enzymes involved in disease processes such as cancer, inflammation, and microbial infections. The incorporation of a fluorine atom, known for its ability to increase metabolic stability, adds an additional layer of interest in the development of potential therapeutic agents.

The compound also plays a significant role in the development of agrochemicals. The trifluoromethyl group is known to enhance the activity of herbicides and pesticides by improving their persistence and effectiveness against a range of pests. By modifying the structure of 5-fluoro-2-(trifluoromethyl)benzenamine, researchers can design new agrochemicals with improved efficacy, selectivity, and environmental compatibility. This makes the compound a valuable building block in the agrochemical industry for the development of next-generation pest control agents.

In materials science, compounds featuring fluorine and trifluoromethyl groups, including 5-fluoro-2-(trifluoromethyl)benzenamine, are used as precursors to high-performance polymers and coatings. The presence of these electronegative groups contributes to the stability, thermal resistance, and chemical durability of the materials. This makes them suitable for applications in harsh environments, such as in the aerospace and electronics industries, where materials need to withstand extreme conditions while maintaining their integrity and functionality.

The compound's potential for further functionalization also enhances its value. The amino group present in 5-fluoro-2-(trifluoromethyl)benzenamine offers the opportunity to engage in a variety of chemical reactions, including nucleophilic substitution, acylation, and coupling reactions, which can lead to the formation of more complex molecules with diverse properties.

Despite its many promising applications, further research is required to fully understand the compound's biological and chemical properties. Studies are ongoing to explore its interactions with biological systems, its potential therapeutic uses, and its role in the development of advanced materials. Furthermore, its safety profile must be thoroughly evaluated before it can be widely used in commercial applications, particularly in the pharmaceutical and agrochemical industries.

In summary, 5-fluoro-2-(trifluoromethyl)benzenamine is a versatile compound with important applications in medicinal chemistry, agrochemicals, and materials science. Its unique structural features, including the fluorine and trifluoromethyl groups, make it a valuable intermediate for the development of bioactive molecules, high-performance materials, and effective pest control agents. Its continued exploration in scientific research may lead to new and innovative applications in various industries.

References

2011. Plant coumarins: VII. Amination of oreoselone trifluoromethanesulfonate. Russian Journal of Organic Chemistry, 47(9).
DOI: 10.1134/s1070428011090235