126301-59-5

Usage

Chemical structure

1-(2′-methoxyethyl)imidazole is composed of an imidazole ring with a 2-methoxyethyl group attached at the 1-position.

Basic properties

The presence of the imidazole ring in the molecule imparts it with basic properties.

Building block

It is commonly used as a building block in organic synthesis.

Catalyst

It is used as a catalyst in various chemical reactions.

Pharmaceutical and agrochemical synthesis

Due to its basic properties, it is useful in the synthesis of pharmaceuticals and agrochemicals.

Solubility

The methoxyethyl group provides the compound with solubility in various organic solvents.

Stability

The methoxyethyl group also contributes to the stability of the compound in organic solvents.

Versatility

It is a versatile chemical for use in research and industrial applications due to its solubility, stability, and basic properties.

Industrial applications

It is used in the chemical industry for various purposes, including the synthesis of pharmaceuticals and agrochemicals.

Research applications

It is also valuable in research due to its versatility and ability to act as a building block and catalyst in organic synthesis.

Upstream product

• 288-32-4 1H-imidazole 
• 6482-24-2 2-Bromoethyl methyl ether 
• 17178-10-8 2-methoxy-ethyl p-toluenesulfonyloxy ester 
• 627-42-9 2-chloroethyl methyl ether 

Relevant academic research and scientific papers

Synthesis and crystal structures of sterically tuned ether functionalized NHC-silver(I) complexes: Antibacterial and nucleic acid interaction studies

A series of new imidazolium salts (1-4) as N-heterocyclic carbene (NHC) precursors have been synthesized by successive N-alkylation method. Reactions of these salts with Ag2O by varying the metal to salt ratio forms a series of new Ag(I)-NHC co

Low-melting zwitterion: Effect of oxyethylene units on thermal properties and conductivity

An imidazolium-based zwitterion containing two oxyethylene units was obtained as a colorless liquid at room temperature. The equimolar mixture of the liquid zwitterion and lithium bis(trifluoromethylsulfonyl)amide showed an ionic conductivity of over 10-4 S cm-1 at 80 °C, which was higher than those of mixtures composed of analogous solid zwitterions.

NHC-silver(I) complexes as chemical nucleases; Synthesis, crystal structures, and antibacterial studies

A series of N-heterocyclic carbene (NHC) precursors, 1-methoxylethyl-3- allylimidazolium hexafluorophosphate (1), 1-ethyl-3-allylimidazolium hexafluorophosphate (2), and 1-pentyl-3-allylimidazolium hexafluorophosphate (3) were synthesized. These salts were treated with Ag2O to afford their corresponding mononuclear Ag(I)-NHC complexes, namely 1-methoxylethyl-3- allylimidazolium silver(I) hexafluorophosphate (4), 1-ethyl-3-allylimidazolium silver(I) hexafluorophosphate (5), and 1-pentyl-3-allylimidazolium silver(I) hexafluorophosphate (6), respectively. These compounds were characterized by physicochemical and spectroscopy techniques. Compounds 4 and 5 were structurally characterized by single crystal X-ray diffraction, and their stability in solution was investigated and found to be acceptable for the antibacterial studies. These new NHC precursors and their respective Ag-NHC complexes were screened for their antibacterial activities against Staphylococcus aureus (ATCC 12600) and Escherichia coli (ATCC 25922). Compounds 1-3 showed no inhibition, whereas 4-6 inhibited the growth of these bacteria. The nuclease activities of the reported compounds against plasmid DNA and RNA were assessed by gel electrophoresis, and the results indicate that complexes 5 and 6 can degrade both DNA and RNA in the absence of an oxidant.

New dual functionalized zwitterions and ionic liquids; Synthesis and cellulose dissolution studies

New dual functionalized N-oxyethylene-N-sulfopropyl imidazolium based ionic liquids (ILs) with unconventional anions for cellulose dissolution were synthesized and characterized (NMR, IR, HRMS, TGA, Td). The ILs were applied in studies on cellulose (MCC) dissolution. Results showed that varying the IL cation had greater impact on cellulose dissolution ability than the minor effect seen by anion exchange. Up to 20 wt-% MCC was dissolved in DMF/ILs solutions at 100 °C. The dual functionalized ionic liquids (ILs) were synthesized via the corresponding N-oxyethylene imidazolium sulfonate zwitterions (ZIs), which were prepared (74–99%) through a double N-imidazole alkylation procedure, including 1,3-propanesultone ring opening. The original MCC and the regenerated cellulose samples were characterized by XRD analysis.

Synthesis of Poly(silyl ether)s by Rhodium(I)-NHC Catalyzed Hydrosilylation: Homogeneous versus Heterogeneous Catalysis

The preparation of 1-(3-triisopropoxysilylpropyl)-3-(2-methoxyethyl)-imidazolium bromide or chloride salts and their reaction with [Rh(COD)(μ-OMe)]2 (COD=1,5-cyclooctadiene) to afford the corresponding [Rh(COD)(NHC)X] (X=Br, Cl; NHC=1-(3-triisopropoxysilylpropyl)-3-(2-methoxyethyl)-2-ilydene-imidazol) species is described. These new compounds were used as catalyst precursors for acetophenone hydrosilylation. The higher activity of the rhodium-chlorido complex evidences a clear halide effect in the activation of the catalyst. Immobilization of the catalytic precursor [Rh(COD)(NHC)Cl] on mobile crystalline material 41 (MCM-41) allows for the preparation of the corresponding heterogeneous catalyst. Reduction of acetophenone to PhMeCH-O-SiMe(OSiMe3)2 by hydrosilylation with 1,1,1,3,5,5,5-heptamethyltrisiloxane is effectively catalyzed by both the homogeneous and the heterogeneous catalysts, in which the homogeneous system is the more active. Interestingly, the heterogeneous catalyst is reusable. Both homo- and heterogeneous catalysts are also effective for the copolymerization of terephthalaldehyde and 1,1,3,3,5,5-hexamethyltrisiloxane, which affords the corresponding poly(silyl ether). The catalyst yields the heterogeneous system polymers with higher molecular weights (Mw=94000gmol-1) and a narrow molecular weight distribution (PDI=1.5-1.7).

Optimizing the electrochemical performance of imidazolium-based polymeric ionic liquids by varying tethering groups

We report the synthesis and characterization of a series of novel imidazolium cation and bis(trifluoromethane)sulfonimide anion (TFSI-)-based ionic liquid (IL) model compounds and their corresponding polymeric ionic liquids (PILs) with various

Mixing divalent ionic liquids: effects of charge and side-chains

We have prepared novel divalent ionic liquids (ILs) based on the bis(trifluoromethylsulfonyl)imide anion where two charged imidazolium groups in the cations are either directly bound to each other or linked by a single atom. We assessed the influence of the side-chain functionality and divalency on their physical properties and on the thermodynamics of mixing. The results indicate that shortening the spacer of a divalent IL reduces its thermal stability and increases its viscosity. Mixtures of divalent and monovalent ILs show small but significant deviations from ideality upon mixing. These deviations appear to depend primarily on the (mis)match of the nature and length of the cation side-chain. The non-ideality imposed by mixing ILs with different side-chains appears to be enhanced by the increase in formal charge of the cations in the mixture.

Synthesis, Characterization, Crystal Structures, and Catalytic C-C Coupling and Hydrosilylation Reactions of Palladium(II) Complexes Derived from CNC Pincer-Type N-Heterocyclic Carbenes

A series of pyridine linker containing bis(benz)imidazolium salts serving as precursors to CNC pincer-type N-heterocyclic carbene (NHC) ligands were prepared by successive N-alkylation of the azole core. Binuclear NHC complexes of silver(I) were synthesized by in situ deprotonation of the corresponding (benz)imidazolium salt with silver(I) oxide in acetonitrile at elevated temperature in the dark. Subsequently, pincer-type palladium(II)-NHC complexes were prepared by transmetalation using silver(I)-NHC complexes in acetonitrile at elevated temperatures. All compounds were fully characterized by elemental analysis, FTIR spectroscopy, and 1H and 13C NMR spectroscopy. X-ray diffraction studies on single crystals of three compounds confirmed the distorted square-planar geometry around the palladium(II) center. All complexes are monomeric in nature, and the bis-NHC ligand chelates in the CNC mode. The effective catalytic potentials of the palladium complexes were demonstrated by their high activities in aqueous-phase Suzuki-Miyaura and Heck-Mizoroki cross-coupling reactions of phenylboronic acid and n-butyl acrylate with a range of functionalized bromobenzene derivatives. The former coupling reaction afforded biphenyls in yields of 71-99%, whereas the latter reaction evidenced low yields of the n-butyl cinnamates. Further, all the palladium complexes were studied for their potential in a catalytic hydrosilylation reaction.

Influence of Cation Size and Polarity on Charge Transport in Ionic Liquid Based Electrolytes

Imidazolium-based ionic liquids (ILs) with allyl and ether side chains were synthesized and characterized. Comprehensive structural and photoelectrochemical characterizations were performed, transport properties of ILs were also examined as electrolyte components in dye sensitized solar cells (DSSCs). The properties of synthesized materials and DSSC performances were compared with 1-propyl-3-methyl imidazolium iodide (PMII) and 1-allyl-3-ethyl imidazolium iodide (AEII) as reference ILs. Ionic conductivities, diffusion coefficients and charge transfer resistances of synthesized ionic liquids were investigated on DSSCs by Electrochemical Impedance Spectroscopy (EIS). The diffusion coefficient values of triiodide ions in different ionic liquid-based electrolytes were measured by the means of diffusion limited current density method and found to be 1.75×10?7 cm2 s?1 and 2.05×10?7 cm2 s?1 with corresponding photocurrent densities of 10.38 mAcm?2 and 12.13 mAcm?2 for the reference AEII and PMII based electrolytes, respectively. However, for the electrolytes of 1-(2-methoxyethyl)-3-allyl imidazolium iodide and 1-allyl-3-methyl imidazolium iodide ionic liquids, these values were found to be 0.86×10?7 cm2 s?1 and 0.57×10?7 cm2 s?1 with photocurrent densities of 9.53 mAcm?2 and 8.98 mAcm?2, respectively. Allyl and ether substituted imidazolium ILs exhibited promising results as potential alternative electrolyte materials for DSSCs.

A zwitterionic salt with one sulfonate and two ether functional groups as an additive for lithium-ion battery electrolyte

An imidazolium-based zwitterionic compound bearing two ether groups at the C-1 and C-2 positions and one sulfonate group at the C-3 position of the imidazolium ring was successfully synthesized. The compound was characterized using nuclear magnetic resonance spectroscopy and elemental analysis. The product (2.5 wt%) was added to a commercial electrolyte for lithium-ion batteries containing 1 M LiPF6 in ethylene carbonate, dimethyl carbonate, and ethyl methyl carbonate (1:1:1 by volume). The resulting electrolyte had a slightly higher ionic conductivity in the range 10–70 °C than the model electrolyte, implying that the additive had a beneficial impact, possibly due to the C-2 rather than the C-1 ether group. Cyclic voltammetry analysis indicated that the electrochemical stability of the electrolyte did not change. The effect of the electrolyte additive on the cell's 1C cycling performance was also examined: it was found that a stable discharge capacity was maintained for up to 100 cycles. Fourier transform infrared spectra of complexes formed by the synthesized product and LiPF6 at different ratios showed that the Li+ ions interacted with all the functional groups.