1-Benzyl-3-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide
[CAS# 433337-24-7]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Imidazoles
• Name: 1-Benzyl-3-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide
• Molecular Formula: C₁₃H₁₃F₆N₃O₄S₂
• Molecular Weight: 453.38
• CAS Registry Number: 433337-24-7
• EC Number: 801-374-5
• SMILES: C[N+]1=CN(C=C1)CC2=CC=CC=C2.C(F)(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319
• Safety Statements: P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313

Discovery and Applications

1-Benzyl-3-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide, also known as [BMIM][Tf2N], is a well-known ionic liquid that has attracted much attention due to its unique properties and wide range of applications. The compound belongs to the family of imidazolyl ionic liquids, which are known for their thermal stability, low volatility, and excellent ionic conductivity, making them valuable in various scientific and industrial fields.

The development of ionic liquids, including 1-benzyl-3-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide, began in the mid-20th century and gained significant development in the 1990s as researchers sought environmentally friendly alternatives to traditional solvents. This ionic liquid is synthesized by reacting 1-benzyl-3-methylimidazole with bis(trifluoromethylsulfonyl)imide, and the resulting compound has excellent stability and versatility.

1-Benzyl-3-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide (C13H15F6N3O4S2) has a molecular weight of 469.39 g/mol. It has high thermal and chemical stability, low volatility, and excellent ionic conductivity. The compound is able to dissolve a wide range of substances, making it an ideal solvent for numerous industrial and laboratory processes.

This ionic liquid can be used as a solvent for a variety of organic reactions, providing a non-volatile, recyclable medium that complies with the principles of green chemistry. It is able to dissolve both organic and inorganic compounds, thereby increasing reaction rates and yields, promoting sustainable chemical processes. 1-Benzyl-3-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide is an effective medium for catalytic reactions, especially in homogeneous catalysis. Its ionic properties stabilize reaction intermediates and transition states, thereby improving the efficiency and selectivity of the catalytic process.

The high ionic conductivity and thermal stability of the compound make it suitable for use as an electrolyte in batteries and supercapacitors. It improves the efficiency, safety and lifespan of these energy storage devices, making them more reliable and effective. Due to its excellent solubility and stability, the compound is used in electrochemical sensors, improving their sensitivity and accuracy. This makes it valuable in a variety of analytical and diagnostic applications.

Incorporating this ionic liquid into polymer electrolytes produces materials with high ionic conductivity and mechanical strength. These materials are beneficial for applications such as fuel cells and advanced batteries. This ionic liquid is able to stabilize nanoparticles and promote their uniform distribution, which is very beneficial for the synthesis and processing of nanomaterials. These nanomaterials can be used in catalysis, electronics and medicine.

This ionic liquid is used in extraction processes to separate specific compounds from complex mixtures. Its selectivity and efficiency in dissolving target molecules improves the purity and yield of the extracted substances, making it useful in pharmaceuticals and fine chemicals. The solubility of this ionic liquid allows the separation of gases such as carbon dioxide and hydrogen from gas mixtures. This application is of great significance in industrial processes and environmental management.

The high thermal stability of 1-benzyl-3-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide makes it suitable for use as a heat transfer fluid in high-temperature applications. Their non-volatility reduces the risk of evaporation and environmental contamination.

Ongoing research on this class of ionic liquids aims to further explore their potential in sustainable technologies, advanced materials, and biopolymer processing. Scientists are working to optimize their synthesis, enhance their properties, and expand their applications in various industries.

References

2018. Liquid-liquid equilibria of toluene+n-heptane+{1-benzyl-3-methyl-imidazolium bis(trifluoromethylsulfonyl)imide or 1-benzyl-pyridinium bis(trifluoromethylsulfonyl)imide}. Korean Journal of Chemical Engineering, 35(3).
DOI: 10.1007/s11814-018-0031-y

2019. A Novel Ionic Liquid of [BeMIM] [Tf2N] for Extracting Pesticides Residues in Tea Sample by Dispersive Liquid-Liquid Microextraction. Chromatographia, 82(12).
DOI: 10.1007/s10337-019-03819-5