1333154-10-1 | 3-(3,5-bis(trifluoroMethyl)phenyl)-1H-1,2,4-triazole

CAS:1333154-10-1 | 3-(3,5-bis(trifluoroMethyl)phenyl)-1H-1,2,4-triazole,Description

The compound "3-(3,5-bis(trifluoromethyl)phenyl)-1H-1,2,4-triazole" is a derivative of 1,2,4-triazole, a heterocyclic compound that has been extensively studied due to its interesting chemical properties and potential applications. The presence of the trifluoromethyl groups in the compound suggests that it may have unique physical and chemical characteristics, making it a subject of interest in various chemical research areas.

Synthesis Analysis

The synthesis of triazole derivatives, including those with bis(trifluoromethyl)phenyl groups, often involves the treatment of amino-triazoles with aldehydes or other electrophilic reagents. For instance, the synthesis of new bis-1,2,4-triazole derivatives has been achieved by reacting 4-amino-3-aryl-5-phenyl-4H-1,2,4-triazoles with bis-aldehydes, followed by reduction to afford the corresponding derivatives. Additionally, the synthesis of bis(trifluoromethyl) phenyl-triazole-pyridine hybrids has been performed using a click chemistry approach, starting with palladium-catalyzed cross-coupling and subsequent alkylation.

Molecular Structure Analysis

The molecular structure of triazole derivatives can be confirmed through various spectroscopic methods such as IR, NMR, and mass spectrometry. For example, the structure of a methyl derivative of a novel 1,4-bis(3,5-dialkyl-4H-1,2,4-triazol-4-yl)benzene was confirmed by X-ray analysis. Single-crystal X-ray structuring has also been used to support the formation of cocrystals of energetic salts of trinitromethyl-substituted triazoles.

Chemical Reactions Analysis

Triazole compounds can undergo a variety of chemical reactions. For instance, the reaction of 3,5-bis(trifluoromethyl)-1,3,4-oxadiazole with primary amines can produce 4-substituted-3,5-bis(trifluoromethyl)-4H-1,2,4-triazoles. Furthermore, the thermal reaction of 3,5-bis(trifluoromethyl)-1H-1,2,4-triazole with alkynes, alkenes, and diazomethane has been explored, leading to various addition products.

Physical and Chemical Properties Analysis

The physical and chemical properties of triazole derivatives, such as their thermodynamic properties, can be significantly influenced by the presence of trifluoromethyl groups. The thermodynamic properties, including enthalpies of sublimation and gas-phase basicity of 3,5-bis(trifluoromethyl)-1,2,4-triazole, have been measured and discussed in comparison with other triazoles. The introduction of trifluoromethyl groups has been shown to enhance the electron affinity of aromatic oxadiazole and triazole chromophores, as evidenced by the study of luminescent copoly(aryl ether)s containing these segments10 .

Scientific Research Applications

Synthesis and Bio-Evaluation in Medicinal Chemistry

A study by Jha and Ramarao (2017) explored the synthesis of novel 1,2,3-triazole-2,4-bis(trifluoromethyl) phenyl pyridine hybrids using the click chemistry approach. These compounds showed promising in vitro activity against bacterial pathogens like Escherichia coli, Salmonella typhimurium, and Staphylococcus aureus, as well as fungal strains such as Aspergillus niger, Fusarium solani, and Penicillium notatum. Some derivatives even outperformed standard drugs like Ciprofloxacin and Griseofulvin against certain bacteria and fungi, highlighting their potential in medicinal chemistry (Jha & Ramarao, 2017).

Metal Complex Formation and Ligand Properties

Stucky et al. (2008) investigated 3,5-Bis(2-hydroxyphenyl)-1H-1,2,4-triazole based ligands, focusing on their protonation and metal complex formation. This research is significant in understanding how these ligands interact with metals, which can be crucial in various fields including catalysis and material science. The study demonstrated that these ligands can form complexes with metals like iron, providing insights into their chemical behavior and potential applications (Stucky et al., 2008).

Enhancement of Electron Affinity in Polymer Chemistry

Chen and Chen (2004) explored the impact of trifluoromethyl groups in aromatic oxadiazole and triazole chromophores on enhancing electron affinity. They synthesized copoly(aryl ether)s consisting of bis(3-(trifluoromethyl) phenyl)-1,3,4-oxadiazole or bis(3-(trifluoromethyl)phenyl)-4-(4-hexyloxyphenyl)-4H-1,2,4-triazole segments. The study is significant in the field of polymer chemistry, especially in the development of materials with specific optical and electrochemical properties (Chen & Chen, 2004) .

Thermodynamic Properties and Basicity

Tipping et al. (1994) measured the thermodynamic properties (like enthalpies of sublimation and gas-phase basicity) of 3,5-bis(trifluoromethyl)-1,2,4-triazole. Their findings are crucial in understanding the fundamental properties of this compound, which can be applied in various scientific fields such as material science and pharmaceutical research (Tipping et al., 1994).

Corrosion Inhibition

Bentiss et al. (2007) investigated the use of 4H-triazole derivatives, including 3,5-bis(trifluoromethyl)-4H-1,2,4-triazole, for corrosion and dissolution protection of mild steel in hydrochloric acid solution. This study is particularly relevant in the field of corrosion science, providing insights into the development of more efficient and environmentally friendly corrosion inhibitors (Bentiss et al., 2007).

Safety And Hazards

The safety data sheet for “3,5-Bis(trifluoromethyl)phenyl isocyanate” indicates that it is a combustible liquid that causes skin irritation, serious eye irritation, and may cause respiratory irritation. It is harmful if swallowed, in contact with skin, or if inhaled.

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