250358-46-4

Basic information

• Product Name: 1-ethyl-3-methylimidazol-3-ium,hydroxide
• Synonyms: 1-Ethyl-3-methylimidazolium hydroxide; EMIM OH
• CAS NO: 250358-46-4
• Molecular Formula: C₆H₁₂N₂O
• Molecular Weight: 128.17200
• Mol File: 250358-46-4.mol

Chemical Properties

• CAS DataBase Reference: 1-ethyl-3-methylimidazol-3-ium,hydroxide(CAS DataBase Reference)
• NIST Chemistry Reference: 1-ethyl-3-methylimidazol-3-ium,hydroxide(250358-46-4)
• EPA Substance Registry System: 1-ethyl-3-methylimidazol-3-ium,hydroxide(250358-46-4)

Safety Data

• Hazardous Substances Data: 250358-46-4(Hazardous Substances Data)

Usage

Uses

Used in Electrochemical Processes:
1-Ethyl-3-methylimidazol-3-ium, hydroxide is used as a solvent or electrolyte in electrochemical processes for its stability and conductivity. It plays a crucial role in facilitating the transfer of electrons and ions, making it an essential component in various electrochemical reactions and devices.
Used in Biotechnology and Pharmaceuticals:
1-Ethyl-3-methylimidazol-3-ium, hydroxide is being studied for its potential applications in biotechnology and pharmaceuticals. Its unique properties and chemical structure make it a promising candidate for use in drug delivery systems, biocatalysts, and other biotechnological processes.
Used in Organic Synthesis and Catalysis:
1-Ethyl-3-methylimidazol-3-ium, hydroxide is used as a powerful base in organic synthesis and catalysis. Its ability to accept protons and participate in acid-base reactions makes it a valuable reagent in the synthesis of various organic compounds and the catalysis of chemical reactions.
Used in Industrial and Scientific Applications:
Due to its unique chemical structure and properties, 1-ethyl-3-methylimidazol-3-ium, hydroxide is a promising candidate for various industrial and scientific applications. Its potential uses include the development of new materials, the improvement of existing processes, and the exploration of novel chemical reactions and phenomena.

Upstream product

• 65039-08-9 3-ethyl-1-methyl-1H-imidazol-3-ium bromide 
• 65039-09-0 1-ethyl-3-methyl-1H-imidazol-3-ium chloride 
• 35935-34-3 1-ethyl-3-methylimidazolium iodide 
• 616-47-7 1-methyl-1H-imidazole 
• 64-67-5 diethyl sulfate 

Downstream Products

• 412009-61-1 1-ethyl-3-methylimidazolium sulphate 
• 145022-44-2 1-ethyl-3-methylimidazolium triflate 
• 174899-65-1 3-ethyl-1-methyl-1H-imidazol-3-ium 2,2,2-trifluoroacetate 
• 663199-29-9 1-ethyl-3-methylimidazolium ethyl ethylphosphonate 
• 1612259-41-2 C₆H₁₁N₂⁽¹⁺⁾*C₈H₁₆NO₃S^(1-) 

Relevant articles and documents

Anion amphiprotic ionic liquids as protic electrolyte matrices allowing sodium metal plating

The sodium-ion battery (SIB) is proposed as a complementary technology to today's commercially dominant lithium-ion battery (LIB). While much know-how can be transferred from LIBs to SIBs, adjustments are still necessary, not the least for the electrolytes employed. Here the use of anion amphiprotic ionic liquid (AAIL) based electrolytes is proposed for SIB application. Two different AAILs, based on organic trifluoromethylsulfonylamide (TFSAm) and inorganic HSO4- anions, respectively, doped with NaTFSI salt have been studied, focusing on electrochemical stability and transport properties, complemented by studies of the ion-ion interactions, and final sodium-ion battery performance via stripping/plating vs. sodium metal electrodes.

Zeolite structure direction by simple bis(methylimidazolium) cations: The effect of the spacer length on structure direction and of the imidazolium ring orientation on the 19F NMR resonances

A series of doubly charged structure-directing agents based on two methylimidazolium moieties linked by a linear bridge of n = 3,4,5, or 6 methylene groups has been used in the synthesis of pure silica zeolites in the presence of fluoride. All of them yielded zeolite TON while only the one with n = 4 was able to produce also zeolite MFI at highly concentrated conditions. In this MFI zeolite, two distinct 19F MAS NMR resonances with about equal intensity were observed, indicating two different chemical environments for occluded fluoride. With the singly charged 1-ethyl-3-methylimidazolium cation, which can be formally considered as the monomer of the bis-imidazolium cation with n = 4, TON and MFI were also obtained, and again two 19F MAS NMR resonances now with largely dissimilar intensities were observed in MFI. Molecular mechanics simulations support a commensurate structure-direction effect for n = 4 in MFI, with each imidazolium ring, in two different orientations, sitting close to the [41526 2] cage. Periodic DFT calculations suggest that F in MFI resides always in the [415262] cages, with the different 19F resonances observed being due to the different orientation of the closest imidazolium ring.

Ionic parachor and its application II. Ionic liquid homologues of 1-alkyl-3-methylimidazolium Propionate {[Cnmim][Pro] (n = 2-6)}

Five propionic acid ionic liquids (PrAILs) [Cnmim][Pro] (n = 2-6) (1-alkyl-3-methylimidazolium propionate) have been prepared by the neutralization method and characterized by 1H NMR spectroscopy and differential scanning calorimetry

Density, Viscosity, and Refractive Index of Ionic Liquid Mixtures Containing Cyano and Amino Acid-Based Anions

In this work, mixtures of five ionic liquids (ILs) based on a common cation, 1-ethyl-3-methylimidazolium ([C2mim]+), and amino acid anions, namely glycinate ([Gly]a), l-alaninate ([l-Ala]a), taurinate ([Tau]a), l-serinate ([l-Ser]a), and l-prolinate ([l-Pro]a) with 1-ethyl-3-methylimidazolium tricyanomethane, [C2mim][C(CN)3], were prepared. The thermophysical properties, namely density, viscosity, and refractive index, of the neat ILs and their mixtures were measured in the temperature range of T = (293.15 up to 353.15) K. The thermal expansion coefficients were calculated for the neat ILs and were considered to be independent of temperature in the working temperature range. Overall, experimental density, viscosity, and refractive index data of the neat AAILs were in a good agreement with those reported in literature. A dramatic decrease in the viscosity was observed for the IL mixtures as the [C2mim][C(CN)3] content increased. The obtained results indicate that mixing [C2mim][C(CN)3] with amino acid-based ILs is a potential mean to further increase flexibility and the fine-tune capacity of the physical and chemical properties of amino acid-based ILs.

Intrinsically electrochromic ionic liquids based on vanadium oxides: Illustrating liquid electrochromic cells

Five intrinsically electrochromic ionic liquids based on vanadium oxides are obtained by a simple and efficient acid base neutralization of the cation hydroxide and ammonium vanadate. These novel ionic liquids play the role of the electrochrome and electrolyte in liquid electrochromic cells.

A non-phosgene process for bioderived polycarbonate with high molecular weight and advanced property profile synthesized using amino acid ionic liquids as catalysts

The conversion of biomass and carbon dioxide to plastics is one of the key solutions to reduce the greenhouse effect and alleviate the petroleum resource depletion. However, there is still a lack of bioderived polymers with high molecular weights and excellent performance and their corresponding green synthesis processes, which limits the potential of bioderived polymers to replace petroleum-based polymers. In this study, an eco-friendly synthetic process for bioderived polycarbonate, catalyzed by amino acid ionic liquids, was developed by utilizing isosorbide (ISO) and diphenyl carbonate (DPC) as reactants, derived from a renewable resource and carbon dioxide, respectively. By using 1-ethyl-3-methylimidazole lysine ([Emim][Lys]) as a catalyst, poly(isosorbide carbonate) (PIC) with the weight average molecular weight of 150 000, the highest reported so far to the best of our knowledge, was synthesized, and the Tg of PIC was up to 174 °C. The reaction mechanism was investigated using nuclear magnetic resonance (NMR) spectroscopy, matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-ToF MS), and density functional theory (DFT) calculation. The remarkable catalytic performance was attributed to the fact that [Emim][Lys] could effectively activate the hydroxyl group of ISO and carbonyl group of DPC, and inhibit the formation of cyclic intermediates. Moreover, to overcome the brittleness of PIC, 1,4-butanediol (BD) and 1,4-cyclohexanedimethanol (CHDM) were introduced into PIC, and the copolycarbonate showed excellent Young's modulus, ultimate tensile strength, and elongation at break, which were 979 MPa, 57 MPa, and 145%, respectively, and were comparable to the commercial petroleum-based polycarbonates. Such a process provides further industrial prospects for the next generation of bioderived polycarbonate.

Novel ionic liquids composed of only azole ions

Novel ionic liquids (ILs) composed of azole type cation and anion were prepared. Triazole and tetrazole were coupled with 1-ethyl-3-methylimidazolium hydroxide. Obtained tetrazole salt was liquid at room temperature showing only glass transition temperature at -89°C. The ionic conductivity reached to 8.9 × 10-3 S cm-1 at room temperature reflecting low viscosity of 42.5 cP at 25°C. This is the first report on the ILs based on only azole type ions.

Synthesis and characterization of imidazolium perrhenate ionic liquids

A series of air- and water-stable imidazolium perrhenate-based room-temperature ionic liquids [(RT)ILs] of the type [Cnmim][ReO 4] (Cnmim = 1-CnH2n+1-3- methylimidazolium, n = 2, 4, 5, 6, 8, 10, 12) have been synthesized and characterized by 1H and 13C NMR spectroscopy, IR spectroscopy, electrospray ionization mass spectrometry (ESI-MS), and elemental analysis (EA). The effect of the variation of the alkyl chain length on physical properties such as melting point, thermal stability, density, and conductivity was examined.

1-Ethyl-3-methylimidazolium tartrate chiral ionic liquids: preparation, characterization and opportunities thereof

A unified acid/base synthetic access to tartrate-based chiral ionic liquids relying on the generation of cation hydroxide salts with AgOH was challenged with the preparation of sensitive 1-ethyl-3-methylimidazolium derivatives. Systematic variation of the starting tartaric acid stoichiometry and configuration led to eight stereoisomeric 1-ethyl-3-methylimidazolium hydrogen tartrate or di-(1-ethyl-3-methylimidazolium)tartrate entities. These salts were all characterised as proper ionic liquids. An unprecedented influence of the configuration ((2S,3S), or (2R,3R) vs. racemic or meso) on dynamic viscosity was observed. The relevance of such tartrate salts as task-specific ionic liquids was demonstrated in a synthetically useful base-promoted intramolecular cyclisation of a C2-symmetrical bis-epoxide en route to the total synthesis of phytofuran metabolites.

Evaluation of imidazolium-based ionic liquids towards vermicidal activity: In vitro & in silico studies

A series of six different ionic liquids (ILs) of the kind 1-alkyl-3-methylimidazolium bromide/hydroxide (IL-Br and IL-OH) tailored with different N-alkyl side chains (ethyl, butyl, octyl) were synthesized and evaluated for their vermicidal activity against the Indian earthworm, Pheretima posthuma. The percentage of paralysis and mortality of earthworms against ILs were recorded in a dose dependent (at different concentrations 2, 4, 8 and 16 mM) and time dependent manner. The ILs with hydroxide as the counter anion (IL-OH) showed higher vermicidal activity compared to their bromide counterparts (IL-Br). Moreover, the ILs with the longest alkyl chain (octyl) were observed to have significant vermicidal activity compared to the rest (ethyl and butyl) as well as the standard drug, Albendazole. Furthermore, theoretical modeling was carried out to visualize the preferential docking positions of these ILs into the active site of β-tubulin. Fascinatingly, it was found that the ILs with longest alkyl side chain showed remarkable vermicidal activity compared to the rest, and the molecular docking studies not only validated the experimental results, but also showed per-residue interaction analysis between the ILs and the different components of β-tubulin.