536755-29-0

Usage

Uses

Used in Pharmaceutical Applications:
1,3-Bis(methyl)imidazolium-2-carboxylate is used as a pharmaceutical agent for its antimicrobial, anti-inflammatory, and anti-cancer properties, offering potential therapeutic benefits in treating various diseases and conditions.
Used in Materials Science:
In the field of materials science, 1,3-Bis(methyl)imidazolium-2-carboxylate is used as a component in the development of new materials with specific properties, such as corrosion inhibition, making it valuable for applications in industries that require protection against corrosion.
Used in Coordination Chemistry:
1,3-Bis(methyl)imidazolium-2-carboxylate is utilized as a ligand in coordination chemistry, contributing to the formation of coordination compounds with unique properties and potential applications in various areas.
Used in Energy Storage Devices:
1,3-Bis(methyl)imidazolium-2-carboxylate is examined as a potential electrolyte in energy storage devices such as batteries and supercapacitors, due to its ability to enhance the performance and efficiency of these systems.
Used in Organic Synthesis and Catalysis:
In the realm of organic synthesis and catalysis, 1,3-Bis(methyl)imidazolium-2-carboxylate serves as a catalyst or a reagent, facilitating chemical reactions and improving the yield of desired products.

Upstream product

• 124-38-9 carbon dioxide 
• 79917-88-7 1,3-dimethylimidazolium chloride 
• 616-47-7 1-methyl-1H-imidazole 
• 616-38-6 carbonic acid dimethyl ester 
• 67-56-1 methanol 
• 4333-62-4 1,3-dimethylimidazolim iodide 
• 1035441-79-2 2-ethoxycarbonyl-1,3-dimethylimidazolium hydrogensulfate 

Downstream Products

• 121091-36-9 2-diphenylphosphine-N,N-dimethylimidazolium chloride 
• 1009105-59-2 1,3-dimethylimidazolium-2-N-(p-chlorophenyl)amidate 
• 1009105-58-1 1,3-dimethylimidazolium-2-N-(3,5-dichlorophenyl)thioamidate 
• 1211417-77-4 (1,3-dimethylimidazol-2-ylidene)borane 
• 77381-68-1 N,N-dimethylimidazolium perchlorate 
• 945017-57-2 1,3-dimethyl-1H-imidazol-3-ium hydrogen carbonate 

Relevant academic research and scientific papers

N -Heterocyclic carbenes on close-packed coinage metal surfaces: Bis-carbene metal adatom bonding scheme of monolayer films on Au, Ag and Cu

By means of scanning tunnelling microscopy (STM), complementary density functional theory (DFT) and X-ray photoelectron spectroscopy (XPS) we investigate the binding and self-assembly of a saturated molecular layer of model N-heterocyclic carbene (NHC) on Cu(111), Ag(111) and Au(111) surfaces under ultra-high vacuum (UHV) conditions. XPS reveals that at room temperature, coverages up to a monolayer exist, with the molecules engaged in metal carbene bonds. On all three surfaces, we resolve similar arrangements, which can be interpreted only in terms of mononuclear M(NHC)2 (M = Cu, Ag, Au) complexes, reminiscent of the paired bonding of thiols to surface gold adatoms. Theoretical investigations for the case of Au unravel the charge distribution of a Au(111) surface covered by Au(NHC)2 and reveal that this is the energetically preferential adsorption configuration.

1,3-Dimethylimidazolium-2-carboxylate: The unexpected synthesis of an ionic liquid precursor and carbene-CO2 adduct

1,3-Dimethylimidazolium-2-carboxylate is formed in good yield, rather than the anticipated organic salt, 1,3-dimethyl-imidazolium methyl carbonate, as the reaction product resulting from both N-alkylation and C-carboxylation of 1-methylimidazole with dime

Highly Modular Piano-Stool N-Heterocyclic Carbene Iron Complexes: Impact of Ligand Variation on Hydrosilylation Activity

The piano-stool configuration combined with N-heterocyclic carbene (NHC) ligation constitutes an attractive scaffold for employing iron in catalysis. Here, we have expanded this scaffold by installing a pentamethyl cyclopentadienyl (Cp*) ligand as a strong electron donor compared to the traditionally used unsubstituted cyclopentadiene (Cp). Moreover, decarboxylation is introduced as a method to prepare these iron(II) NHC complexes, which avoids the isolation of air-sensitive free carbenes. In addition to the Cp/Cp? variation, the complexes have been systematically modulated at the NHC scaffold, the NHC wingtip groups, and the ancillary ligands in order to identify critical factors that govern the catalytic activity of the iron center in the hydrosilylation of aldehydes. These modulations reveal the importance of steric tailoring and optimization of electron density for high catalytic performance. The data demonstrate a critical role of the NHC scaffold with triazolylidenes imparting consistently higher activity than imidazolylidenes and a correlation between catalytic activity and steric rather than electronic factors. Moreover, the implementation of steric bulk is strongly dependent on the nature of the NHC and severely limited by the Cp? iron precursor. The best performing catalytic systems reach turnover frequencies, TOFmax's, of up to 360 h-1 at 60 °C. Mechanistic investigations by 1H NMR and in situ IR spectroscopies indicate a catalyst activation that involves CO release and aldehyde coordination to the [Fe(Cp)(NHC)I] fragment.

Thermally Activated n-Doping of Organic Semiconductors Achieved by N-Heterocyclic Carbene Based Dopant

Molecular doping plays an important role in the modification of carrier density of organic semiconductors thus enhancing their optoelectronic performance. However, efficient n-doping remains challenging, especially owing to the lack of strongly reducing and air-stable n-dopants. Herein, an N-heterocyclic carbene (NHC) precursor, DMImC, is developed as a thermally activated n-dopant with the excellent stability in air. Its thermolysis in situ regenerates free NHC and subsequently dopes typical organic semiconductors. In sequentially doped FBDPPV films, DMImC does not disturb the π–π packing of the polymer and achieves good miscibility with the polymer. As a result, a high electrical conductivity of up to 8.4 S cm?1 is obtained. Additionally, the thermally activated doping and the excellent air stability permit DMImC to be noninteractively co-processed with polymers in air. Our results reveal that DMImC can be served as an efficient n-dopant suitable for various organic semiconductors.

Application of N-heterocyclic carbene and carbene precursor as n-type dopant in semiconductor materials

The invention discloses application of N-heterocyclic carbene and a carbene precursor as an n-type dopant in semiconductor materials. The N-heterocyclic carbene and the carbene precursor can be used as a stable and efficient n-type dopant of a solution to

Sterically controlling 2-carboxylated imidazolium salts for one-step efficient hydration of epoxides into 1,2-diols

In order to overcome the disadvantages of excessive water and many byproducts in the conventional process of epoxide hydration into 1,2-diols, 2-carboxylated imidazolium salts were first adopted as efficient catalysts for one-step hydration of epoxides into 1,2-diols. By regulating the cation chain lengths, different steric structures of 2-carboxylated imidazolium salts with chain lengths from C1 to C4 were prepared. The salt with the shortest substituent chain (DMIC) exhibited better thermal stability and catalytic performance for hydration, achieving nearly 100% ethylene oxide (EO) conversion and 100% ethylene glycol (EG) selectivity at 120 °C, 0.5 h with just 5 times molar ratio of H2O to EO. Such a tendency is further confirmed and explained by both XPS analysis and DFT calculations. Compared with other salts with longer chains, DMIC has stronger interaction of CO2?anions and imidazolium cations, exhibiting a lower tendency to release CO2?and form HO-CO2?, which can nucleophilically attack and synergistically activate ring-opening of epoxides with imidazolium cations. The strong huge sterically dynamic structure ring-opening transition state slows down the side reaction, and both cations and anions stabilized the transition state imidazolium-EG-HO-CO2?, both of which could avoid excessive hydration into byproducts, explaining the high 1,2-diol yield. Based on this, the cation-anion synergistic mechanism is then proposed.

A substituent- And temperature-controllable NHC-derived zwitterionic catalyst enables CO2upgrading for high-efficiency construction of formamides and benzimidazoles

Chemocatalytic upgrading of the greenhouse gas CO2 to valuable chemicals and biofuels has attracted broad attention in recent years. Among the reported approaches, N-formylation of CO2 with an amine is of great significance due to its versatility in the construction of N-containing linear and cyclic skeletons. Herein, a stable N-heterocyclic carbene-carboxyl adduct (NHC-CO2) was facilely prepared and could be used as a recyclable zwitterionic catalyst for efficient CO2 reductive upgrading via either N-formylation or further coupling with cyclization under mild conditions (25 °C, 1 atm CO2) using hydrosilane as a hydrogen source. More than 30 different alkyl and aromatic amines could be transformed into the corresponding formamides or benzimidazoles with remarkable yields (74%-98%). The electronic effect of the introduced substituent on NHC-CO2 was found to evidently affect the thermostability and nucleophilicity of the zwitterionic catalyst, which is directly correlated with its catalytic activity. Moreover, NHC-CO2 could supply CO2 by in situ decarboxylation at a specific temperature that is dependent on the introduced substituent type. Experimental and computational studies showed that the carboxyl species on NHC-CO2 was not only a nucleophilic center, but also a C1 source which rapidly captures or substitutes ambient CO2 during hydrosilylation. In addition, a simple and green conceptual process was designed for the product purification and catalyst recycling, with a good feasibility for small-scale production.

MANUFACTURE METHOD OF N-HETEROCYCLIC CARBENE COMPLEX COMPOUND, N-HETEROCYCLIC CARBENE COMPLEX COMPOUND PRODUCED BY THE SAME, AND METHOD FOR DELAYING POLYMERIZATION OF POLYURETHANE USING THE SAME

The present invention relates to solid N - heterocyclic carbene complexes which are delay catalysts for polyurethane polymerization. More specifically N - heterocyclic carbene is synthesized, and carbon dioxide (CO) is synthesized on a synthesized N - heterocyclic carbene. 2 The adduct of N - heterocyclic carbene complex, which is a solid, coordinated with any one of zinc (Zn), tin (Sn), and magnesium (Mg) salts salt, can solve the problem of the availability of N - heterocyclic carbene complexes. When the polyurethane polymerization proceeds at room temperature to 60 °C or more, the polyurethane polymerization reaction is initiated, so that the polyurethane polymerization reaction can be effectively performed by delaying polymerization of the polyurethane.

Cooperation of N-Heterocyclic Carbenes on a Gold Surface

Atomically precise tailoring of interface structures is crucial for developing functional materials. We demonstrate an N-heterocyclic carbene (NHC) based molecular tool, which modifies the structure of a gold surface with atomic accuracy by the formation of gold nanorods. After adsorption on the gold surface, individual surface atoms are pulled out by the NHCs, generating single-atom surface defects and mobile NHC-Au species. Atomistic calculations reveal that these molecular “ballbots” can act as assembling tools to dislocate individual surface atoms. The predicted functionality of these carbene-based complexes is confirmed by scanning tunneling microscopy measurements. Cooperative operation of these NHC-Au species induces a step-wise formation of gold nanorods. Consequently, the surface is re-structured by a zipper-type mechanism. Our work presents a foundation to utilize molecular-based nanotools to design surface structures.

PRODUCTION METHOD FOR AMIDATE COMPOUND

A method for producing an amidate compound represented by Formula (3), comprising reacting a urethane compound represented by Formula (1) with a carboxylate compound represented by Formula (2): (in the formulas, A, n, R1, R2, R3, R4, R5, R6, X, and a are as described in the Description).