1-Benzyl-3-methylimidazolium chloride, CAS: 36443-80-8

Key Applications:

Solvent and Reaction Medium

• Serves as a polar, non‑volatile ionic medium for organic synthesis, particularly in transformations benefiting from enhanced cation–π interactions.
• Supports transition‑metal‑catalyzed reactions, including cross‑coupling and C–N/C–C bond‑forming processes, where the benzyl substituent can influence solvation and catalyst stability.
• Useful in phase‑transfer–like environments due to its strong chloride coordination and tunable viscosity.

Catalysis and Organocatalysis

• Functions as a co‑catalyst or catalytic medium in acid‑promoted and nucleophilic substitution reactions.
• Enhances rates of electrophilic aromatic substitutions and benzylation reactions by stabilizing reactive intermediates.
• Employed in supported ionic liquid phase (SILP) catalytic systems, where the aromatic cation improves immobilization on carbonaceous supports.

Materials Science and Polymer Processing

• Acts as a structure‑directing additive in polymerization and copolymerization systems, influencing morphology and ionic conductivity.
• Used in the preparation of polymer electrolytes and ion‑conductive films where the benzyl group contributes to mechanical rigidity and cation mobility.
• Supports dispersion and stabilization of carbon nanomaterials, including CNTs and graphene derivatives, through π–π interactions.

Electrochemical Applications

• Serves as a component in electrolyte formulations for electrochemical devices requiring high ionic strength and chloride availability.
• Applied in electrode surface modification and electrocatalyst preparation, where the aromatic cation can modulate interfacial charge transfer.

Extraction, Separation, and Purification

• Effective in liquid–liquid extraction systems for metal ions and organic solutes, leveraging chloride coordination and aromatic interactions.
• Used in chromatographic stationary phase modification to enhance selectivity for aromatic and polar analytes.

Antimicrobial and Biochemical Research

• Investigated as a cationic antimicrobial agent in microbiological studies, where the benzyl substituent enhances membrane interaction.
• Utilized in protein and enzyme stabilization studies due to its tunable hydrophobicity and ionic strength contribution.

General Laboratory Utility

• Suitable as a precursor for synthesizing other benzyl‑functionalized ionic liquids via anion exchange.
• Employed in formulation studies exploring viscosity, polarity, and solvation effects across imidazolium IL families.

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