367-25-9 | 2,4-Difluoroaniline

CAS:367-25-9 | 2,4-Difluoroaniline,Description

2,4-Difluoroaniline is a chemical compound that is part of the aniline family, characterized by the presence of two fluorine atoms attached to the benzene ring. While the provided papers do not directly discuss 2,4-difluoroaniline, they do provide insights into the synthesis and properties of related fluorinated aromatic compounds and amino acids, which can be informative for understanding the broader context of fluorinated chemistry.

Synthesis Analysis

The synthesis of fluorinated compounds is a topic of interest due to their potential applications in medicinal chemistry and materials science. For instance, the synthesis of fluorinated amino acids such as (2S,3S)-4,4,4-trifluorovaline and (2S,4S)-5,5,5-trifluoroleucine involves a series of steps starting from a fluorinated carboxylic acid, followed by the formation of a chiral oxazoline and subsequent oxidative rearrangement to a dihydro-2H-oxazinone. Similarly, the synthesis of perfluoro-tert-butyl 4-hydroxyproline amino acids involves a Mitsunobu reaction, which is a key step in introducing a perfluoro-tert-butyl group. These methods highlight the complexity and precision required in synthesizing fluorinated compounds, which could be analogous to the synthesis of 2,4-difluoroaniline.

Molecular Structure Analysis

The molecular structure of fluorinated compounds is significantly influenced by the presence of fluorine atoms. For example, in the case of 2'-deoxy-2',4'-difluoroarabinose-modified nucleic acids, the introduction of fluorine at the 4' position induces a strong bias toward the North conformation of the sugar pucker, which is different from the typical South/East conformation steered by a 2'-βF. This demonstrates how fluorine substitution can affect the molecular conformation and, by extension, the properties of the molecule.

Chemical Reactions Analysis

Fluorinated compounds participate in various chemical reactions that are often unique due to the influence of fluorine. The gem-difluorination of methylenecyclopropanes (MCPs) leading to the synthesis of gem-difluorocyclobutanes is an example of a reaction that proceeds via a Wagner-Meerwein rearrangement, showcasing the reactivity of fluorinated intermediates under mild conditions. Additionally, the metalation of N-(pivaloyl)- and N-(tert-butoxycarbonyl)difluoroanilines shows regiocontrol by fluorine atoms during the synthesis of carboxylic derivatives, indicating the directing effect of fluorine in chemical reactions.

Physical and Chemical Properties Analysis

The physical and chemical properties of fluorinated compounds are often distinct from their non-fluorinated counterparts due to the high electronegativity and small size of fluorine. For instance, the incorporation of perfluoro-tert-butyl groups into amino acids results in distinct conformational preferences and sensitivity in 19F NMR, which can be exploited in probes and medicinal chemistry. The thermal stability and RNase H substrate activity of 2',4'-difluoroarabino-modified nucleic acids also illustrate the impact of fluorine on the stability and biological activity of these molecules.

Scientific Research Applications

Quantum Chemical Applications

Computational Studies and Non-Linear Optical (NLO) Applications 2,4-Difluoroaniline has been a subject of quantum chemical computational studies. Notably, its hyperpolarizability, frontier molecular orbital analysis, and NBO data have been analyzed using Density Functional Theories (DFT). The compound has shown promising potential for NLO applications due to its high chemical hardness, indicating stability, and significant electrophilicity index. This makes 2,4-difluoroaniline a noteworthy candidate in the field of non-linear optics (Antony Selvam et al., 2020).

Spectroscopic Analysis and Electronic Structure Studies

Vibrational Analysis and Spectroscopic Studies Comprehensive vibrational analysis of 2,4-Difluoroaniline has been performed using theoretical and experimental FTIR as well as FT-Raman spectral data. Such studies have been essential in understanding the effect of substituted F atoms on the aromatic ring. These investigations also extend to the analysis of geometrical and electronic structure, with recorded UV–Vis spectra providing insights into the electronic properties, such as frontier orbitals and band gap energies. Non-linear optical properties have been calculated, predicting the NLO behavior of the compound. Such studies contribute to a deeper understanding of the molecular properties of 2,4-Difluoroaniline (Pathak et al., 2014) .

Environmental and Material Science Applications

Aerobic Biodegradation Performance 2,4-Difluoroaniline has been studied for its aerobic biodegradation performance. The biodegradability and dynamic analysis of this compound provide essential insights, especially when considering the treatment of fluoroanilines containing wastewater along with domestic sewage. Such studies are pivotal for environmental science, aiding in the development of effective biodegradation methods for potentially harmful compounds (Qi, 2007).

Ophthalmic Lens Polymer Additives The compound has been utilized in the manufacturing of functional ophthalmic lenses. When used as an additive, 2,4-Difluoroaniline contributes to the physical and optical characteristics of copolymerized ophthalmic lenses, particularly in UV-blocking applications. Such applications underscore the compound's relevance in material sciences, especially in the creation of specialized medical devices (No & Sung, 2014).

Safety And Hazards

2,4-Difluoroaniline is classified as a combustible liquid. It is harmful if swallowed and toxic in contact with skin. It is recommended to avoid breathing its dust, fume, gas, mist, vapors, or spray. Use of this compound should be in a well-ventilated area, away from heat, sparks, open flames, and hot surfaces.

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