320-51-4 | 4-Chloro-alpha,alpha,alpha-trifluoro-m-toluidine

CAS:320-51-4 | 4-Chloro-alpha,alpha,alpha-trifluoro-m-toluidine,Description

4-Chloro-3-(trifluoromethyl)aniline is a chemical compound that has been the subject of various studies due to its potential applications in materials science and as an intermediate in the synthesis of pharmaceuticals and agrochemicals. The compound is characterized by the presence of a chloro and a trifluoromethyl group attached to an aniline moiety, which significantly influences its chemical and physical properties.

Synthesis Analysis

The synthesis of related compounds has been explored in several studies. For instance, a method for synthesizing 3-chloro-4-[1,1,2-trifluoro-2-(trifluoromethoxy)-ethoxy]aniline starting from 3,4-dichloronitrobenzene has been reported, with a high overall yield of 72% and minimal environmental pollution. Another study describes the practical synthesis of 3-chloro-4-(3-fluorobenzyloxy)aniline, which features readily available starting materials and an 82% yield, suggesting a robust and scalable process suitable for industrial production. These methods highlight the feasibility of synthesizing chloro-trifluoromethyl aniline derivatives with high efficiency.

Molecular Structure Analysis

The molecular structure of chloro-trifluoromethyl aniline derivatives has been extensively studied using various spectroscopic techniques and theoretical calculations. For example, the conformational study of a complex containing a trifluoromethoxy-aniline derivative revealed that the trifluoromethoxy group is nearly perpendicular to the arene ring, and the amino group is eclipsed by a chromium carbonyl bond. Vibrational spectroscopy and quantum chemical studies on 2-chloro-5-(trifluoromethyl)aniline provided insights into the influence of chlorine substituents on the molecule's vibrational wavenumbers and the delocalization of electron density within the molecule.

Chemical Reactions Analysis

The reactivity of chloro-trifluoromethyl aniline derivatives has been explored in the context of synthesizing novel compounds. For instance, 4-chloro-3-(trifluoroacetyl)coumarin, a related compound, was used as a building block for the synthesis of 7-(trifluoromethyl)-6H-chromeno[4,3-b]quinolin-6-ones, showcasing the versatility of chloro-trifluoromethyl aniline derivatives in organic synthesis.

Physical and Chemical Properties Analysis

The physical and chemical properties of chloro-trifluoromethyl aniline derivatives are influenced by the presence of electron-withdrawing groups such as chloro and trifluoromethyl. These groups affect the molecule's electron distribution, vibrational spectra, and thermodynamic parameters. Studies have shown that these substituents can lead to interesting properties, such as potential usefulness in nonlinear optical (NLO) materials, as evidenced by the vibrational analysis and theoretical computations of 4-chloro-3-(trifluoromethyl)aniline and its bromo and fluoro analogs. The detailed interpretation of vibrational spectra and the analysis of hyperconjugation interactions, HOMO-LUMO energy gap, and molecular electrostatic potential surfaces contribute to a deeper understanding of these properties.

Scientific Research Applications

Nonlinear Optical Materials

4-Chloro-3-(trifluoromethyl)aniline has been investigated for its potential application in nonlinear optical (NLO) materials. Research conducted through experimental and theoretical vibrational analysis, including Fourier Transform-Infrared and Fourier Transform-Raman techniques, suggests its significance in this field. The study explores the impact of electron-donating and withdrawing effects on the structure and vibrational spectra of this compound, providing insights into its utility for NLO materials (Revathi et al., 2017).

Vibrational Spectroscopic Analysis

Vibrational spectroscopic analysis, particularly using Fourier-transform infrared and FT-Raman spectra, has been performed on 4-Chloro-3-(trifluoromethyl)aniline. This research includes quantum chemical calculations and studies of first-order hyperpolarizability, HOMO-LUMO studies, and insights into its microscopic non-linear optical behavior. Such studies are essential for understanding the chemical and physical properties of this compound (Arivazhagan et al., 2012).

Intermediate in Pesticides and Herbicides

4-Chloro-3-(trifluoromethyl)aniline serves as an intermediate in the manufacturing of efficient, low-toxicity pesticides and new herbicides. The synthesis methods and the characteristics of the resultant pesticides and herbicides are significant areas of study, highlighting its industrial applications (Zhou Li-shan, 2002).

Synthesis of 7-(trifluoromethyl)-6H-chromeno[4,3-b]quinolin-6-ones

The compound is utilized as a novel building block in the synthesis of 7-(trifluoromethyl)-6H-chromeno[4,3-b]quinolin-6-ones. This involves reactions with commercially available anilines and provides a new avenue for chemical synthesis, demonstrating its versatility in organic chemistry (Iaroshenko et al., 2011).

Safety And Hazards

4-Chloro-3-(trifluoromethyl)aniline is toxic if inhaled, harmful if swallowed, and harmful in contact with skin. It causes skin irritation and serious eye irritation.

Future Directions

The highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) energies were predicted to interpret the orbital overlapping and the possibility of charge transfer within the molecule using the B3LYP method with 6-31G (d,p) basis set combination.

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