1-Allyl-3-methylimidazolium chloride
[CAS# 65039-10-3]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ionic liquid
• Name: 1-Allyl-3-methylimidazolium chloride
• Synonyms: 1-Ally-3-methylimidazolium chloride
• Molecular Formula: C₇H₁₁N₂.Cl
• Molecular Weight: 158.63
• CAS Registry Number: 65039-10-3
• EC Number: 629-635-7
• SMILES: C[N+]1=CN(C=C1)CC=C.[Cl-]

Properties

• Melting point: 55 °C^*
• Refractive index: 1.540 (50 °C)^**

^* Sakizadeh, Kumars

^** Chen, Ye

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

1-Allyl-3-methylimidazolium chloride, commonly abbreviated as [AMIM][Cl], is an ionic liquid that has attracted much attention for its unique properties and wide range of applications. The compound belongs to the broad class of imidazolyl ionic liquids, which are liquids at room temperature.

The discovery of 1-allyl-3-methylimidazolium chloride was part of a broad exploration of ionic liquids that began in the mid-20th century. Researchers were interested in developing new solvents that could overcome the limitations of traditional organic solvents. [AMIM][Cl] is synthesized by the alkylation of 1-methylimidazolium with allyl chloride, resulting in a stable, low-melting ionic liquid.

The molecular formula of 1-allyl-3-methylimidazolium chloride is C7H11ClN2. Key properties include: stability at high temperatures, making it suitable for a variety of industrial processes; negligible vapor pressure, which minimizes environmental emissions; it can dissolve a wide range of organic and inorganic compounds; and it has high ionic conductivity, which is beneficial for electrochemical applications.

One of the main applications of [AMIM][Cl] is as a solvent in chemical synthesis. Its ability to dissolve a wide range of compounds makes it useful in catalysis, organic synthesis, and polymerization reactions. The unique ionic environment can increase reaction rates and selectivity, leading to more efficient processes.

[AMIM][Cl] has been studied for its potential in biomass processing, particularly in the dissolution and pretreatment of cellulose. Its ability to break down cellulose into its constituent sugars makes it a valuable tool for the production of biofuels and biochemicals. This application is consistent with the growing interest in renewable energy and sustainable materials.

The high ionic conductivity of [AMIM][Cl] makes it suitable for electrochemical applications, including electrolytes in batteries and supercapacitors. It can improve the performance and lifetime of these devices by providing a stable ionic environment for charge transfer.

In the field of green chemistry, [AMIM][Cl] is valued for its environmental benefits. It can replace volatile organic solvents, reduce harmful emissions, and improve workplace safety. Its recyclability and reusability further promote sustainable chemical practices.

[AMIM][Cl] is also used as a catalyst for a variety of chemical reactions. Its ionic properties can provide unique catalytic properties, increasing reaction efficiency and yield. This application extends to a range of industrial processes from petrochemicals to pharmaceuticals.

The use of [AMIM][Cl] supports environmental sustainability by reducing reliance on hazardous organic solvents. Its low volatility and recycling potential make it a more environmentally friendly alternative for many chemical processes.

The non-flammability and thermal stability of [AMIM][Cl] improve safety in industrial and laboratory environments. It reduces the risk of accidents and contributes to safer chemical handling practices.

[AMIM][Cl] is versatile and can be used in a variety of applications from synthesis to electrochemistry. Its wide range of utility highlights its importance in modern chemical research and industry.

References

Ning Sun, Mustafizur Rahman, Ying Qin, Mirela L. Maxim, Héctor Rodríguez and Robin D. Rogers. Complete dissolution and partial delignification of wood in the ionic liquid 1-ethyl-3-methylimidazolium acetate, Green Chem., 2009, 11, 646.