1-(2-Trifluoromethylphenyl)imidazole

Overview

1-(2-Trifluoromethylphenyl)imidazole is a chemical compound that belongs to the class of imidazole derivatives. Imidazoles are heterocyclic compounds containing a five-membered ring composed of three carbon atoms and two nitrogen atoms at non-adjacent positions. The presence of a trifluoromethyl group on the phenyl ring of this compound imparts unique chemical properties, making it of interest in various fields such as medicinal chemistry and materials science.

Chemical Structure and Properties

The chemical formula of 1-(2-Trifluoromethylphenyl)imidazole is C10H7F3N2. The structure consists of an imidazole ring attached to a phenyl ring, which is further substituted with a trifluoromethyl group at the ortho position. The trifluoromethyl group is known for its electron-withdrawing properties, which can influence the reactivity and stability of the compound.

Physical Properties

- Molecular Weight: 212.17 g/mol - Appearance: Typically a white to off-white crystalline solid - Melting Point: Approximately 80-85°C - Solubility: Soluble in organic solvents such as ethanol, methanol, and dichloromethane

Chemical Properties

The presence of the trifluoromethyl group can enhance the lipophilicity of the compound, which may affect its biological activity and pharmacokinetics. The imidazole ring can participate in hydrogen bonding and coordination with metal ions, making it a versatile ligand in coordination chemistry.

Synthesis

The synthesis of 1-(2-Trifluoromethylphenyl)imidazole can be achieved through various methods. A common approach involves the condensation of 2-trifluoromethylbenzaldehyde with an imidazole derivative under acidic or basic conditions. Catalysts such as Lewis acids or bases may be employed to facilitate the reaction.

Applications

1-(2-Trifluoromethylphenyl)imidazole has potential applications in several areas:

- Medicinal Chemistry: The compound can serve as a scaffold for the development of pharmaceuticals, particularly those targeting enzymes or receptors where the imidazole moiety is a key pharmacophore. - Materials Science: Due to its unique electronic properties, it may be used in the design of advanced materials, including polymers and liquid crystals. - Coordination Chemistry: As a ligand, it can form complexes with transition metals, which may have applications in catalysis or as functional materials.

Safety and Handling

As with many chemical compounds, appropriate safety measures should be taken when handling 1-(2-Trifluoromethylphenyl)imidazole. It should be stored in a cool, dry place, and protective equipment such as gloves and goggles should be worn to prevent skin and eye contact.

Also see

- Imidazole - Trifluoromethyl group - Medicinal chemistry - Coordination chemistry