521304-36-9

Basic information

• Product Name: 1,3-Dimethylimidazolium methanesulfonate
• Synonyms: 1,3-Dimethylimidazolium methanesulfonate;MMIM CH3SO3;[C1MIm]MS
• CAS NO: 521304-36-9
• Molecular Formula: C6H12N2O3S
• Molecular Weight: 192.23608
• Product Categories: Chemical Synthesis;Imidazolium;Ionic Liquids;Specialty Synthesis
• Mol File: 521304-36-9.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,3-Dimethylimidazolium methanesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Dimethylimidazolium methanesulfonate(521304-36-9)
• EPA Substance Registry System: 1,3-Dimethylimidazolium methanesulfonate(521304-36-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• Hazardous Substances Data: 521304-36-9(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
1,3-Dimethylimidazolium methanesulfonate is utilized as a catalyst to facilitate various organic reactions, enhancing their efficiency and selectivity. Its unique chemical structure allows it to stabilize reactive intermediates and transition states, thereby improving the overall yield and quality of synthesized products.
Used in Ionic Liquid Solvent Applications:
As an ionic liquid solvent, 1,3-Dimethylimidazolium methanesulfonate is employed for dissolving a wide range of compounds, particularly those that are poorly soluble in traditional solvents. Its ability to dissolve both polar and non-polar substances makes it a valuable asset in processes requiring high solvation capabilities.
Used in Electrochemistry:
1,3-Dimethylimidazolium methanesulfonate is used as an electrolyte in electrochemical applications, such as in batteries and fuel cells, due to its favorable electrochemical properties and stability over a broad temperature range.
Used in Biomass Processing:
In the biomass processing industry, 1,3-Dimethylimidazolium methanesulfonate is used as a solvent for the dissolution and pretreatment of lignocellulosic materials, which is crucial for the efficient conversion of biomass into valuable chemicals and biofuels.
Used in Pharmaceuticals:
1,3-Dimethylimidazolium methanesulfonate is explored for its potential use in the pharmaceutical sector, where it can serve as a reaction medium for the synthesis of active pharmaceutical ingredients or as a component in drug delivery systems, leveraging its unique solvation and catalytic properties to improve drug synthesis and efficacy.
Overall, 1,3-Dimethylimidazolium methanesulfonate's multifaceted utility across different industries stems from its combination of chemical, physical, and environmental advantages, solidifying its status as a green and effective compound for contemporary applications.

InChI:InChI=1/C5H9N2.CH4O3S/c1-6-3-4-7(2)5-6;1-5(2,3)4/h3-5H,1-2H3;1H3,(H,2,3,4)/q+1;/p-1

Upstream product

• 616-47-7 1-methyl-1H-imidazole 
• 616-42-2 dimethylsulfite 
• 4333-62-4 1,3-dimethylimidazolim iodide 
• 75-75-2 methanesulfonic acid 
• 66-27-3 Methyl methanesulfonate 

Relevant articles and documents

A simple halide-to-anion exchange method for heteroaromatic salts and ionic liquids

A broad and simple method permitted halide ions in quaternary heteroaromatic and ammonium salts to be exchanged for a variety of anions using an anion exchange resin (A- form) in non-aqueous media. The anion loading of the AER (OH- form) was examined using two different anion sources, acids or ammonium salts, and changing the polarity of the solvents. The AER (A- form) method in organic solvents was then applied to several quaternary heteroaromatic salts and ILs, and the anion exchange proceeded in excellent to quantitative yields, concomitantly removing halide impurities. Relying on the hydrophobicity of the targeted ion pair for the counteranion swap, organic solvents with variable polarity were used, such as CH3OH, CH3CN and the dipolar nonhydroxylic solvent mixture CH3CN:CH2Cl 2 (3:7) and the anion exchange was equally successful with both lipophilic cations and anions.

IONIC LIQUID CONTAINING ALLYLSULFONATE ANION

PROBLEM: Providing a novel ionic liquid, which is low-cost, environment-friendly, and has low viscosity and melting point. MEANS FOR SOLVING THE PROBLEM: The present invention is the invention of the ionic liquid represented by the general formula [1]: {wherein, R1 to R3 and n pieces of R4 each independently represent hydrogen atom or alkyl group having 1 to 4 carbon atoms, R5 to R7 each independently represent alkyl group, aralkyl group, or aryl group, R8 represents alkyl group, aralkyl group, aryl group, or the one represented by the general formula [2]: (wherein T represents alkylene chain having 1 to 8 carbon atoms, n represents 1 or 2, and R1 to R7 are the same as the above-described), X represents nitrogen atom or phosphorus atom, n represents 1 or 2. When n is 1, R3 and R4 are bound and may form cyclohexene ring together with the adjacent carbon atoms. In addition, when X is nitrogen atom, R5 to R7 or R5 to R6 may form hetero ring with nitrogen atom binding thereto}.

Imidazolium ionic liquids: A simple anion exchange protocol

An efficient and simple protocol was developed to obtain quantitative iodide or bromide exchange for a broad range of anions in imidazolium ionic liquids. Selected anions were loaded in an anion exchange resin using two different procedures and were then used to provide a pure convenient ion pair. The Royal Society of Chemistry 2009.

1-Alkyl-3-methylimidazolium alkanesulfonate ionic liquids, [C nH2n+1mim][CkH 2k+1SO3]: Synthesis and physicochemical properties

A set of 1-alkyl-3-methylimidazolium alkanesulfonate ionic liquids, [C nmim][CkSO3], formed by the variation of the alkyl chain lengths both in the cation and the anion (n = 1-6, 8, or 10; k = 1-4, or 6), was synthesised, with sixteen of them being novel. The ionic liquids were characterised by 1H and 13C NMR spectroscopy, and mass spectrometry. Their viscosities and densities as a function of temperature, as well as melting points and decomposition temperatures, were determined. The molecular volumes, both experimental and calculated, were found to depend linearly on the sum (n + k). the Owner Societies 2009.

Process for the Preparation of Onium Alkylsulfonates

The invention relates to a process for the preparation of onium alkylsulfonates by reaction of an onium halide or carboxylate with a symmetrically substituted dialkyl sulfite or with an asymmetrically substituted dialkyl sulfite at temperatures of 50 to 170° C.

Method of preparation of halogen-free ionic liquids and ionic liquids prepared in this manner

The reaction of N-alkylimidazol with alkyl sulfonates, at room temperature, favors the production of 1,3-dialkylimidazolium alkane-sulfonates as crystalline solids at high yields. The alkane-sulfonate anions may be easily substituted by a series of other anions [BF4, PF6, PF3(CF2CF3)3, CF3SO3 and (CF3SO2)2N] through simple anion, salt, or acid reactions in water at room temperature. The extraction with dichloromethane, filtration, and evaporation of the solvent, allows the production of the desired ionic liquids at a yield of 80-95%. The purity of these ionic liquids (in some cases >99.4%) is performed using the intensity of 13C satellite signals from the magnetic resonance spectrums of the N-methyl imidazolium group as an internal standard.

A simple and practical method for the preparation and purity determination of halide-free imidazolium ionic liquids

The reaction of N-alkylimidazole with alkyl sulfonates at room temperature affords 1,3-dialkylimidazolium alkanesulfonates as crystalline solids in high yields. The alkanesulfonate anions can be easily substituted by a series of other anions [BF4, PF6, PF3(CF 2CF3)3, CF3SO3 and N(CF3SO2)2] by simple reaction of anions, salts, or acids in water at room temperature. Extraction with dichloromethane, filtration through a short basic alumina column and solvent evaporation affords the desired ionic liquids in 80-95% yield. The purity (> 99.4%) of these ionic liquids can be determined by 1H NMR spectra using the intensity of the 13C satellites of the imidazolium N-methyl group as internal standard.

Ionic liquids as reaction media for esterification of carboxylate sodium salts with alkyl halides

Ionic liquids based on 1,3-dialkylimidazolinium methanesulfonate have been used as effective reusable reaction media in the esterification of several carboxylate sodium salts with different alkyl halides. Products are easily isolated by extraction with ether, and the protocol is mild and green, compared to the existing methods based on toxic solvents. Proper 'design' of the ionic liquid allows us to obtain esters always in quantitative yields.