1-Butyl-2,3-dimethylimidazolium bis(trifluoromethanesulfonyl)imide
[CAS# 350493-08-2]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Imidazoles
• Name: 1-Butyl-2,3-dimethylimidazolium bis(trifluoromethanesulfonyl)imide
• Synonyms: bis(trifluoromethylsulfonyl)azanide;1-butyl-2,3-dimethylimidazol-3-ium
• Molecular Formula: C₁₁H₁₇F₆N₃O₄S₂
• Molecular Weight: 433.39
• CAS Registry Number: 350493-08-2
• EC Number: 700-236-0
• SMILES: CCCCN1C=C[N+](=C1C)C.C(F)(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F

Properties

• Density: 1.4059 g/cm³
• Melting point: -76 °C
• Boiling point: 430 °C
• Flash point: 110 °C

Safety Data

• Hazard Symbols: GHS05;GHS06;GHS07 Danger
• Risk Statements: H301-H314-H315-H319
• Safety Statements: P260-P264-P264+P265-P270-P280-P301+P316-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P351+P338-P305+P354+P338-P316-P321-P330-P332+P317-P337+P317-P362+P364-P363-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin corrosion	Skin Corr.	1	H314
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	3	H301

• Transport Information: UN 2922

Discovery and Applications

1-Butyl-2,3-dimethylimidazolium bis(trifluoromethanesulfonyl)imide (BMMIM-TFSI) is an ionic liquid that has attracted great interest due to its unique properties and wide range of applications. As a member of imidazolium-based ionic liquids, BMMIM-TFSI exhibits excellent thermal stability, low volatility, and high ionic conductivity.

The development of BMMIM-TFSI can be traced back to the ongoing exploration of ionic liquids in the late 20th and early 21st centuries. Researchers aimed to create ionic liquids with specific cation and anion combinations to tailor their properties for various applications. The synthesis of BMMIM-TFSI involves the combination of 1-butyl-2,3-dimethylimidazolium cation (BMMIM⁺) with bis(trifluoromethanesulfonyl)imide anion (TFSI⁻). This combination yields a stable ionic liquid with desirable properties.

The synthesis of BMMIM-TFSI generally follows a two-step process: The synthesis begins with the alkylation of 1-methylimidazole with a butyl halide such as butyl bromide or chloride to form 1-butyl-2,3-dimethylimidazolium halide (BMMIM halide). The BMMIM halide is then reacted with lithium bis(trifluoromethanesulfonyl)imide (LiTFSI) to replace the halide ion with the TFSI anion, yielding BMMIM-TFSI.

The primary application of BMMIM-TFSI is as an electrolyte in electrochemical devices such as batteries, supercapacitors, and fuel cells. Its high ionic conductivity and thermal stability make it an excellent choice for enhancing the performance and safety of these devices. BMMIM-TFSI is particularly useful in lithium-ion batteries, where it can improve ion transport and overall efficiency.

BMMIM-TFSI is an effective solvent in a variety of chemical reactions, including organic synthesis and catalysis. Its ability to dissolve a wide range of compounds, coupled with its stability, makes it suitable for high-temperature and long-duration reactions. Researchers have used BMMIM-TFSI for the synthesis of pharmaceuticals, fine chemicals, and polymers.

As an ionic liquid, BMMIM-TFSI contributes to green chemistry, providing an environmentally friendly alternative to traditional organic solvents. Its low volatility and non-flammability reduce the risk of air pollution and harmful emissions. BMMIM-TFSI is used in sustainable processes, such as biomass conversion and CO2 capture, in line with efforts to develop more sustainable industrial practices.

BMMIM-TFSI is used as a lubricant and additive in various mechanical and industrial applications. Its stability under extreme conditions makes it suitable for high-performance lubrication, reducing friction and wear in machinery. In addition, it is used as an additive in polymers and coatings to enhance their performance and durability.

In separation processes, BMMIM-TFSI is adopted for its excellent solubility properties. It is used in liquid-liquid extraction and gas absorption to effectively separate complex mixtures. This ability is particularly useful in drug purification and industrial wastewater treatment.

References

2018. Copper-Catalyzed Reactions in Organic Synthesis. Chemical Reviews, 118(17).
DOI: 10.1021/acs.chemrev.8b00092