1-Allyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide
[CAS# 655249-87-9]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Imidazoles
• Name: 1-Allyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide
• Synonyms: bis(trifluoromethylsulfonyl)azanide 1-methyl-3-prop-2-enylimidazol-1-ium
• Molecular Formula: C₉H₁₁F₆N₃O₄S₂
• Molecular Weight: 403.32
• CAS Registry Number: 655249-87-9
• EC Number: 663-153-8
• SMILES: C[N+]1=CN(C=C1)CC=C.C(F)(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H319
• Safety Statements: P264+P265-P280-P305+P351+P338-P337+P317

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315

Discovery and Applications

1-Allyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide, commonly referred to as [AMIM][Tf2N], is an important member of the imidazolyl family of ionic liquids. The unique properties of this ionic liquid, such as its thermal stability, low volatility, and excellent ionic conductivity, make it highly valuable in a variety of scientific and industrial applications.

The discovery of [AMIM][Tf2N] stems from the broader development of ionic liquids, which began in the mid-20th century but gained significant momentum in the 1990s. Researchers were motivated by the search for environmentally friendly alternatives to volatile organic solvents. The synthesis of [AMIM][Tf2N] involves the alkylation of 3-methylimidazole with allyl chloride followed by ion exchange with lithium bis(trifluoromethylsulfonyl)imide. This process produces an ionic liquid with strong thermal and chemical stability.

1-Allyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide (C10H13F6N3O4S2) has a molecular weight of 403.34 g/mol. It is characterized by high thermal stability, low vapor pressure, and high ionic conductivity. These properties make it an excellent candidate for a variety of applications, especially in the fields of green chemistry and electrochemistry.

[AMIM][Tf2N] is used as a solvent for a variety of organic reactions, providing a non-volatile and recyclable medium. Its ability to dissolve a wide range of organic and inorganic compounds increases reaction rates and yields, contributing to more sustainable chemical processes. This ionic liquid is an effective medium for catalytic reactions, especially in homogeneous catalysis. Its ionic nature stabilizes reaction intermediates and transition states, thereby improving the efficiency and selectivity of catalytic processes.

Due to its high ionic conductivity and thermal stability, [AMIM][Tf2N] is used as an electrolyte in batteries and supercapacitors. It improves the efficiency, safety, and lifetime of these devices, making them more reliable and effective. The stability and solvation properties of [AMIM][Tf2N] make it suitable for use in electrochemical sensors, thereby improving their sensitivity and accuracy. This application is valuable in various analytical and diagnostic fields.

Incorporation of [AMIM][Tf2N] into polymer electrolytes yields materials with high ionic conductivity and mechanical strength. These materials are beneficial for applications such as fuel cells and advanced batteries. Ionic liquids are able to stabilize nanoparticles and promote their uniform distribution, which is highly advantageous for the synthesis and processing of nanomaterials. These nanomaterials can be used in catalysis, electronics, and medicine.

[AMIM][Tf2N] 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 it to separate 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 [AMIM][Tf2N] makes it suitable for use as a heat transfer fluid in high-temperature applications. Its non-volatility reduces the risk of evaporation and environmental contamination.

Research on 1-allyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide continues to explore its potential in sustainable technologies, advanced materials, and biopolymer processing. Scientists aim to optimize its synthesis, enhance its properties, and expand its applications in various industries.

References

2022. Introduction of Ionic Liquids as Highly Efficient Plasticizers and Flame Retardants of Cellulose Triacetate Films. Journal of Polymers and the Environment, 30(8).
DOI: 10.1007/s10924-022-02407-3

2019. Ecotoxicity evaluation towards Vibrio fischeri of imidazolium- and pyridinium-based ionic liquids for their use in separation processes. SN Applied Sciences, 1(8).
DOI: 10.1007/s42452-019-0916-3

2016. Ionic conductivities of 1-allyl-3-methylimidazolium bis(trifluoromethylsulfonyl)amide. Electrochemistry.
DOI: 10.1007/978-3-642-02723-9_108