2105-61-5 | 1,2,4-Trifluoro-5-nitrobenzene

CAS:2105-61-5 | 1,2,4-Trifluoro-5-nitrobenzene,Description

1,2,4-Trifluoro-5-nitrobenzene is a chemical compound that is part of the broader class of nitrobenzene derivatives, which are characterized by the presence of nitro groups (-NO2) and fluorine atoms attached to a benzene ring. These compounds are of interest due to their diverse applications in the field of organic synthesis, materials science, and as intermediates in the production of pharmaceuticals and agrochemicals.

Synthesis Analysis

The synthesis of fluorinated nitrobenzene derivatives can be complex due to the reactivity of both the nitro and fluoro substituents. For instance, the synthesis of 1,2,4,5-tetrafluorobenzene, a related compound, has been studied using electron diffraction and ab initio calculations, which provide insights into the molecular structure that can influence synthetic routes. The synthesis of 1,2,4-Trifluoro-5-nitrobenzene itself is not directly described in the provided papers, but methods for synthesizing similar compounds often involve halogenation and nitration reactions. For example, 2,3,4-Trifluoronitrobenzene was synthesized from dichlorofluorobenzene through nitration and subsequent fluorination.

Molecular Structure Analysis

The molecular structure of fluorinated nitrobenzenes is influenced by the electron-withdrawing effects of both the nitro and fluorine groups. These effects can lead to unique electronic and steric properties. For example, the structure of 1,3,5-triamino-2,4,6-trinitrobenzene was studied using computational methods, revealing a planar structure with significant push-pull conjugation. Although this compound is not the same as 1,2,4-Trifluoro-5-nitrobenzene, the analysis of electronic structures in similar compounds can provide valuable information about the electronic properties of nitrobenzene derivatives.

Chemical Reactions Analysis

The reactivity of fluorinated nitrobenzenes is influenced by the presence of electron-withdrawing groups, which can affect the course of chemical reactions. For instance, the oxidation-reduction reactions involving nitro groups in trifluoromethanesulfonic acid show that the presence of nitro groups can lead to complex reaction pathways involving hydride transfers and benzylations10 . While this study does not directly involve 1,2,4-Trifluoro-5-nitrobenzene, it highlights the types of reactions that nitro groups can undergo in the presence of other substituents.

Physical and Chemical Properties Analysis

The physical and chemical properties of fluorinated nitrobenzenes are determined by their molecular structure. The presence of fluorine atoms imparts unique properties such as increased stability and lower polarizability compared to their non-fluorinated counterparts. For example, fluorinated polyimides synthesized from related compounds exhibit high thermal stability and low dielectric constants. The crystal structure of 1,3,5-trichloro-2,4,6-trifluorobenzene, another related compound, was determined using X-ray and neutron diffraction, revealing insights into the molecular orientation and internal vibrations. These studies on related compounds can shed light on the expected properties of 1,2,4-Trifluoro-5-nitrobenzene.

Scientific Research Applications

1. Synthesis of Novel Derivatives and Compounds

A study by Sipyagin et al. (2004) explored the synthesis of new derivatives from chloro-nitrobenzene compounds, which could potentially include 1,2,4-trifluoro-5-nitrobenzene analogs. They achieved this through fluorination and perfluoroalkylation, demonstrating the versatility of nitrobenzene derivatives in synthesizing various fluorine-containing compounds (Sipyagin et al., 2004).

2. Studying Molecular Structures and Dynamics

Research by Laerdahl et al. (1998) investigated the rotational motion of adjacent nitro groups in dinitrobenzenes, which might be applicable to understanding the molecular dynamics of 1,2,4-trifluoro-5-nitrobenzene. Their approach involved quantum chemical calculations and X-ray diffraction to explore the intermolecular interactions (Laerdahl et al., 1998).

3. Applications in Environmental Pollution Remediation

A study by Shah (2014) discussed the microbial degradation of chloro-nitrobenzene compounds, which could be relevant for the environmental processing or remediation of 1,2,4-trifluoro-5-nitrobenzene. This research highlighted how certain bacterial strains can utilize nitrobenzene derivatives as energy sources, suggesting potential applications in bioremediation (Shah, 2014).

4. Exploration in Photophysics and Photochemistry

Giussani and Worth (2017) provided insights into the complex photophysics and photochemistry of nitrobenzene, which might extend to the study of 1,2,4-trifluoro-5-nitrobenzene. This research could be significant in understanding the UV absorption and decay paths of such compounds (Giussani & Worth, 2017).

5. Investigating Electrosynthetic Applications

The electrochemical reduction of nitrobenzene derivatives was explored in a study by Du and Peters (2010), which could be applicable to the electrosynthesis of compounds from 1,2,4-trifluoro-5-nitrobenzene. Their research into the reduction of chloroethyl-nitrobenzene at carbon cathodes provides a basis for understanding similar electrochemical processes (Du & Peters, 2010).

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