4-(4-(Trifluoromethyl)-1H-imidazol-2-yl)benzonitrile
[CAS# 33469-11-3]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Imidazoles
• Name: 4-(4-(Trifluoromethyl)-1H-imidazol-2-yl)benzonitrile
• Synonyms: 4-[5-(trifluoromethyl)-1H-imidazol-2-yl]benzonitrile
• Molecular Formula: C₁₁H₆F₃N₃
• Molecular Weight: 237.18
• CAS Registry Number: 33469-11-3
• SMILES: C1=CC(=CC=C1C#N)C2=NC=C(N2)C(F)(F)F

Properties

• Density: 1.4±0.1 g/cm³ Calc.^*
• Boiling point: 412.5±45.0 ºC 760 mmHg (Calc.)^*
• Flash point: 203.3±28.7 ºC (Calc.)^*
• Index of refraction: 1.554 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P271-P280-P302-P304-P305-P313-P332-P337-P338-P340-P351-P352

Discovory and Applicatios

4-(4-(Trifluoromethyl)-1H-imidazol-2-yl)benzonitrile is a chemical compound that contains both an imidazole ring and a benzonitrile group, making it a structurally interesting molecule in the field of medicinal chemistry. This compound has gained attention for its potential applications in various biological and chemical contexts due to its unique structure and functional groups. The trifluoromethyl group on the imidazole ring and the nitrile group attached to the benzene ring are particularly important in modulating the chemical and biological properties of the molecule.

The discovery of compounds like 4-(4-(Trifluoromethyl)-1H-imidazol-2-yl)benzonitrile is part of a broader effort in the pharmaceutical and agrochemical industries to identify molecules with specific and potent activities. The trifluoromethyl group is known to significantly affect the electronic properties of a molecule. This highly electronegative group can enhance the compound's lipophilicity and stability, as well as improve its binding affinity to certain receptors or enzymes. The presence of a trifluoromethyl group can also enhance the molecule's metabolic stability, which is crucial in drug design.

The imidazole ring in this compound contributes to its potential biological activity. Imidazole derivatives have been studied extensively for their antifungal, anticancer, and antimicrobial properties. The ability of the imidazole group to interact with various biological targets, including enzymes and receptors, has made it a valuable building block in drug development. In particular, imidazole-containing compounds can bind to metal ions, such as those in metalloenzymes, making them useful in designing enzyme inhibitors.

The benzonitrile portion of the molecule also plays an essential role in its overall activity. The nitrile group is highly polar and can participate in hydrogen bonding interactions with biological macromolecules. Moreover, the benzonitrile moiety is commonly found in compounds that exhibit antitumor and anti-inflammatory activities. Nitriles are known to have versatile reactivity, and their presence can help in the design of molecules with varied pharmacological effects.

4-(4-(Trifluoromethyl)-1H-imidazol-2-yl)benzonitrile is likely to have applications in the development of new drugs, particularly in the areas of cancer treatment, antimicrobial therapies, and possibly central nervous system disorders. The trifluoromethyl group, in particular, may help optimize the compound's pharmacokinetic properties, improving its bioavailability and selectivity for certain targets. Additionally, the imidazole ring’s ability to coordinate with metal ions suggests potential in designing inhibitors of metalloproteins, such as those involved in cancer progression or antimicrobial resistance.

In terms of synthesis, this compound can be obtained through a variety of synthetic routes that involve the formation of the imidazole ring, introduction of the trifluoromethyl group, and subsequent coupling with the benzonitrile moiety. The trifluoromethyl group can be introduced via electrophilic substitution reactions or other fluorination methods, while the nitrile group is typically introduced through nucleophilic substitution reactions or nitration of a benzene derivative.

Overall, 4-(4-(Trifluoromethyl)-1H-imidazol-2-yl)benzonitrile is a versatile and potentially bioactive compound. Its unique combination of trifluoromethyl, imidazole, and benzonitrile groups makes it an interesting candidate for further study in medicinal chemistry. The compound's structural characteristics offer many possibilities for modification and optimization, making it a valuable scaffold for the development of new therapeutics.