1,2-Dimethyl-3-propylimidazolium bis(trifluoromethylsulfonyl)imide
[CAS# 169051-76-7]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Imidazoles
• Name: 1,2-Dimethyl-3-propylimidazolium bis(trifluoromethylsulfonyl)imide
• Synonyms: bis(trifluoromethylsulfonyl)azanide;1,2-dimethyl-3-propylimidazol-1-ium
• Molecular Formula: C₁₀H₁₅F₆N₃O₄S₂
• Molecular Weight: 419.36
• CAS Registry Number: 169051-76-7
• EC Number: 805-807-9
• SMILES: CCCN1C=C[N+](=C1C)C.C(F)(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H317-H319-H412
• Safety Statements: P261-P264-P264+P265-P270-P272-P273-P280-P301+P317-P302+P352-P305+P351+P338-P321-P330-P332+P317-P333+P317-P337+P317-P362+P364-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin sensitization	Skin Sens.	1	H317
Acute toxicity	Acute Tox.	4	H302
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319

Discovery and Applications

1,2-Dimethyl-3-propyl imidazolium bis(trifluoromethylsulfonyl)imide is an ionic liquid that has attracted great interest due to its unique properties and wide range of applications. As a member of the imidazolium-based ionic liquid family, this compound is known for its thermal stability, low volatility, and high ionic conductivity.

The exploration of ionic liquids, including 1,2-dimethyl-3-propyl imidazolium bis(trifluoromethylsulfonyl)imide, began in the mid-20th century. The significant increase in interest in the 1990s stemmed from the need for environmentally friendly solvents. This particular ionic liquid was synthesized by combining 1,2-dimethyl-3-propyl imidazolium with bis(trifluoromethylsulfonyl)imide, forming a compound that combines stability and versatility.

The chemical formula of 1,2-dimethyl-3-propyl imidazolium bis(trifluoromethylsulfonyl)imide is C11H17F6N2O4S2, and the molecular weight is 438.38 g/mol. It has excellent thermal and chemical stability, making it suitable for high temperatures and harsh chemical processes. Its ionic nature provides high ionic conductivity, which is beneficial for various electrochemical applications.

The compound is used as a solvent in organic reactions, especially those that require high solubility for both organic and inorganic reactants. Its low volatility reduces environmental emissions and complies with the principles of green chemistry. It can be used as a medium for catalytic reactions, increasing reaction rates and selectivity. The ionic nature of the compound stabilizes transition states and intermediates in the catalytic cycle, thereby improving overall efficiency.

Due to its high ionic conductivity and thermal stability, 1,2-dimethyl-3-propylimidazole bis(trifluoromethylsulfonyl)imide is used as an electrolyte in batteries and supercapacitors. It helps develop energy storage devices with higher efficiency and safety. This ionic liquid is used in various electrochemical devices, such as fuel cells and electrochemical sensors, and its properties can improve performance and durability.

The compound is incorporated into polymer electrolytes to form materials with high ionic conductivity and mechanical strength. These materials are used in advanced batteries, fuel cells, and other electrochemical devices. The compound's ability to stabilize nanoparticles makes it valuable in the synthesis and processing of nanomaterials. These nanomaterials have applications in catalysis, electronics, and medicine.

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

The high thermal stability of 1,2-dimethyl-3-propylimidazole bis(trifluoromethylsulfonyl)imide 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.

The future of 1,2-dimethyl-3-propylimidazole bis(trifluoromethylsulfonyl)imide research lies in further exploring its potential in sustainable technologies, advanced materials, and electrochemical applications. Ongoing research aims to optimize its synthesis, enhance its properties, and expand its applications in various industries.

References

2016. Ionic conductivities of 1,2-dimethyl-3-propylimidazolium bis(trifluoromethylsulfonyl)imide. Electrochemistry.
DOI: 10.1007/978-3-642-02723-9_476

2023. Tutorial for thermal analysis of ionic liquids. Journal of Thermal Analysis and Calorimetry.
DOI: 10.1007/s10973-023-12439-z

2015. Oxygen Reduction Reaction in Ionic Liquids: An Overview. Electrochemistry in Ionic Liquids.
DOI: 10.1007/978-3-319-15132-8_18