N,N'-Dicyclohexylimidazolium tetrafluoroborate
[CAS# 286014-38-8]

Identification

• Name: N,N'-Dicyclohexylimidazolium tetrafluoroborate
• Synonyms: 1,3-Dicyclohexylimidazolium tetrafluoroborate
• Molecular Formula: C₁₅H₂₅N₂.BF₄
• Molecular Weight: 320.18
• CAS Registry Number: 286014-38-8
• EC Number: 626-286-2
• SMILES: [B-](F)(F)(F)F.C1CCC(CC1)N2C=C[N+](=C2)C3CCCCC3

Properties

• Melting point: 174 °C

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
Skin corrosion	Skin Corr.	1C	H314
Serious eye damage	Eye Dam.	1	H318
Acute toxicity	Acute Tox.	4	H302

Discovery and Applications

N,N'-Dicyclohexylimidazolium tetrafluoroborate is an ionic liquid that has gained attention in the field of chemistry due to its unique properties and versatile applications. This compound features a dicyclohexylimidazolium cation paired with a tetrafluoroborate anion, resulting in a highly stable and tunable ionic liquid with distinct characteristics suitable for various industrial and research applications.

The discovery of N,N'-Dicyclohexylimidazolium tetrafluoroborate can be traced back to the growing interest in ionic liquids, which are salts in liquid form at room temperature. Researchers sought to develop ionic liquids with specific properties, such as low viscosity, high thermal stability, and the ability to dissolve a wide range of substances. The choice of the dicyclohexylimidazolium cation was driven by its potential to provide these desirable properties, combined with the tetrafluoroborate anion, which is known for its stability and low reactivity.

The synthesis of N,N'-Dicyclohexylimidazolium tetrafluoroborate involves the reaction of dicyclohexylimidazole with an appropriate fluoroboric acid or its salts. The process typically begins with the preparation of the dicyclohexylimidazole precursor, which is synthesized from cyclohexylamine and imidazole through an alkylation reaction. The resulting dicyclohexylimidazole is then reacted with tetrafluoroboric acid or a tetrafluoroborate salt under controlled conditions to form the ionic liquid. Purification is usually achieved by techniques such as recrystallization or column chromatography to obtain the pure product.

One of the primary applications of N,N'-Dicyclohexylimidazolium tetrafluoroborate is in the field of catalysis. The ionic liquid can act as a solvent and a catalyst in various chemical reactions. Its unique properties, such as high thermal stability and low volatility, make it suitable for use in high-temperature reactions and processes where traditional solvents might decompose or evaporate. It has been employed in reactions such as olefin metathesis, where its ability to stabilize reactive intermediates enhances the efficiency of the catalytic process.

In addition to its role in catalysis, N,N'-Dicyclohexylimidazolium tetrafluoroborate is used in material science for the development of advanced materials. The ionic liquid's ability to dissolve a wide range of substances and its tunable properties make it valuable for creating novel materials with specific characteristics. For example, it has been utilized in the synthesis of ionic liquid-based polymers and composites, which can be tailored for applications in electronics, energy storage, and other high-tech fields.

Another significant application of this ionic liquid is in the extraction and separation of metal ions. Its high stability and solubility in a variety of solvents allow for efficient extraction processes, making it useful in the recovery of valuable metals from ores and waste materials. The ability to selectively extract and separate metal ions enhances its utility in hydrometallurgy and recycling industries.

The advantages of N,N'-Dicyclohexylimidazolium tetrafluoroborate include its high stability, low volatility, and tunable properties, which make it suitable for a wide range of applications. However, challenges may include the need to manage the cost of synthesis and ensure the environmental safety of the ionic liquid. Research continues to focus on improving the efficiency of its synthesis, expanding its applications, and addressing any potential environmental impacts.

Future research on N,N'-Dicyclohexylimidazolium tetrafluoroborate may explore its use in new catalytic processes, advanced material development, and environmental applications. The ongoing study of ionic liquids like this one promises to unlock new possibilities in chemistry and materials science.

References

2021. Metal-Catalyzed Coupling of Aryl- and Hetarylstannanes. Science of Synthesis.
https://science-of-synthesis.thieme.com/app/text/?id=SD-105-00345

2013. Combining Oxidative N-Heterocyclic Carbene Catalysis with Click Chemistry: A Facile One-Pot Approach to 1,2,3-Triazole Derivatives. Chemistry - An Asian Journal.
DOI: 10.1002/asia.201300138

2011. Catalytic Diboration: Conjugate Additions. Science of Synthesis.
https://science-of-synthesis.thieme.com/app/text/?id=SD-201-00191