33468-69-8 | 4-(Trifluoromethyl)-1H-imidazole

CAS:33468-69-8 | 4-(Trifluoromethyl)-1H-imidazole,Description

4-(Trifluoromethyl)-1H-imidazole is a chemical compound that belongs to the class of imidazoles, which are heterocyclic compounds characterized by a five-membered ring containing two nitrogen atoms. The trifluoromethyl group attached to the imidazole ring significantly influences the compound's chemical and physical properties, making it a valuable moiety in various chemical reactions and potential applications in pharmaceuticals.

Synthesis Analysis

The synthesis of 1,2,4-trisubstituted-(1H)-imidazoles, which are closely related to 4-(trifluoromethyl)-1H-imidazole, can be achieved through the Cu(OTf)2- and I2-catalyzed C–C bond cleavage of chalcones and benzylamines. Another synthetic approach involves the van Leusen reaction, which allows for the incorporation of a trifluoromethyl group into 1,4,5-trisubstituted imidazoles using trifluoroacetimidoyl chlorides with tosylmethylisocyanide. Additionally, the synthesis of heterocyclic compounds with a trifluoromethyl moiety and an imidazole ring can be performed by reacting 3-bromo-1,1,1-trifluoroacetone with various heteroarylamines.

Molecular Structure Analysis

The molecular structure of compounds related to 4-(trifluoromethyl)-1H-imidazole has been studied using various spectroscopic methods and theoretical calculations. For instance, the molecular geometry, vibrational frequencies, and NMR chemical shift values of a triazol–imidazol compound were calculated using density functional theory (DFT) and compared with experimental data, showing good agreement. In another study, the planarity of the imidazo[1,2-a]pyridine group and the disorder of the trifluoromethyl group were observed in the crystal structure of a related compound.

Chemical Reactions Analysis

The presence of the trifluoromethyl group in the imidazole ring can influence the reactivity and biological activity of the compound. For example, analogues of 4,5-bis(3,5-dichlorophenyl)-2-trifluoromethyl-1H-imidazole have shown potential as antibacterial agents, with the structure-activity relationship indicating the importance of the imidazole NH and electron-withdrawing groups for activity against MRSA.

Physical and Chemical Properties Analysis

The introduction of a trifluoromethyl group into the imidazole ring can alter the physical and chemical properties of the compound, such as its electronic and spatial structure, as well as its interaction energies between molecules. These properties are crucial for understanding the compound's behavior in various environments and its potential applications in medicinal chemistry.

Scientific Research Applications

Corrosion Inhibition

4-(Trifluoromethyl)-1H-imidazole derivatives exhibit significant potential in corrosion inhibition. For example, derivatives like 4-(4,5-bis(4-methoxyphenyl)-1H-imidazol-2-yl)phenol have been shown to provide up to 96% corrosion inhibition efficiency in certain conditions. These derivatives adhere strongly to surfaces, suggesting their application in protecting metals from corrosion, particularly in acidic environments (Prashanth et al., 2021).

Synthesis and Biological Evaluation

4-(Trifluoromethyl)-1H-imidazole derivatives have been synthesized for various biological evaluations. Studies show these compounds exhibiting promising activities, such as lipase inhibition and antioxidant properties, indicating potential applications in medicinal chemistry (Menteşe et al., 2013) .

Application in Energetic Materials

Compounds based on imidazole derivatives, including 4-(Trifluoromethyl)-1H-imidazole, are explored for their applications in nitrogen-rich gas generators. These compounds, due to their high positive heats of formation and energy contributions from their molecular structures, have potential applications in areas requiring high-energy materials (Srinivas et al., 2014).

Antibacterial Applications

Several 4-(Trifluoromethyl)-1H-imidazole analogs have been investigated for their antibacterial properties. For instance, analogs such as 4,5-bis(3,5-dichlorophenyl)-2-trifluoromethyl-1H-imidazole have shown activity against methicillin-resistant Staphylococcus aureus (MRSA), suggesting their potential as novel antibacterial agents (Antolini et al., 1999).

Nanocomposite and Polymer Applications

4-(Trifluoromethyl)-1H-imidazole derivatives have been used in the synthesis of new fluorinated curing agents for epoxy resins. These agents demonstrate significant improvements in properties like water repellency and thermal stability, indicating their utility in the field of high-performance polymers (Ghaemy et al., 2012).

Electroluminescent Properties

Derivatives of 4-(Trifluoromethyl)-1H-imidazole have been used in the design of efficient fluorescence molecules for electroluminescent applications. These molecules, with specific structural modifications, show stable deep-blue emission, indicating their potential in the development of electronic and photonic devices (Wang et al., 2018).

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