174899-66-2

Usage

Uses

1. Used in Organic Synthesis:
1-Butyl-3-methylimidazolium trifluoromethansulfonate is used as a glycosylation promoter in the synthesis of oligosaccharides from thiophenyl and trichloroacetimidate glycoside donors. This application is due to its ability to facilitate the formation of glycosidic bonds, which are crucial in the synthesis of complex carbohydrate structures.
2. Used in Solvent Extraction:
1-Butyl-3-methylimidazolium trifluoromethansulfonate is used as a solvent for the extraction of sulfur and nitrogen containing aromatic organic compounds from aliphatic hydrocarbons. Its ionic nature allows for effective separation of these compounds based on their polarity and solubility.
3. Used in Polymer Science:
1-Butyl-3-methylimidazolium trifluoromethansulfonate is used as a reagent in the preparation of ion-conductive polymeric membranes. The ionic liquid enhances the ionic conductivity of the resulting polymer membranes, making them suitable for applications such as fuel cells and sensors.
4. Used in Electrolyte Synthesis:
1-Butyl-3-methylimidazolium trifluoromethansulfonate is used as a dopant in the synthesis of poly(ethyl methacrylate) based polymer electrolytes to increase the ionic conductivity. This application takes advantage of the ionic liquid's ability to improve the transport of ions within the polymer matrix.
5. Used in Reaction Medium:
1-Butyl-3-methylimidazolium trifluoromethansulfonate is used as a reaction medium to synthesize aryl ketones by Friedel-Crafts benzoylation of aryl compounds using bismuth triflate as a catalyst. The ionic liquid provides a suitable environment for the reaction to proceed efficiently.
6. Used in Alternative Reaction Conditions:
1-Butyl-3-methylimidazolium trifluoromethansulfonate can be used as an alternative to lithium perchlorate-diethyl ether mixture in the Diels-Alder reaction. This ionic liquid offers a safer and more environmentally friendly alternative for carrying out this important class of reactions in organic chemistry.

InChI:InChI=1/C8H15N2.CHF3O3S/c1-3-4-5-10-7-6-9(2)8-10;2-1(3,4)8(5,6)7/h6-8H,3-5H2,1-2H3;(H,5,6,7)/q+1;/p-1

Upstream product

• 33454-82-9 lithium trifluoromethanesulfonate 
• 79917-90-1 1-butyl-3-methylimidazolium chloride 
• 4316-42-1 1-Butylimidazole 
• 333-27-7 methyl trifluoromethanesulfonate 
• 2926-30-9 sodium triflate 
• 616-47-7 1-methyl-1H-imidazole 
• 109-65-9 1-bromo-butane 
• 2926-27-4 potassium trifluoromethansulfonate 
• 1493-13-6 trifluorormethanesulfonic acid 
• 85100-77-2 1-n-butyl-3-methylimidazolim bromide 
• 916850-37-8 1-butyl-3-methyl-1H-imidazol-3-ium methylcarbonate 
• 149-73-5 trimethyl orthoformate 
• 342789-81-5 1-n-butyl-3-methylimidazolium methanesulfonate 
• 38542-94-8 CF₃O₃S^(1-)*H⁽¹⁺⁾*H₃N 

Downstream Products

• 15144-82-8 3-methoxy-fluoren-9-one 
• 86-73-7 9H-fluorene 
• 166959-36-0 2-benzylphenyl trifluoromethanesulfonate 
• 7254-06-0 3-chloro-fluoren-9-one 
• 1705-89-1 3-methyl-9H-fluoren-9-one 
• 512787-24-5 2-benzoylphenyl trifluoromethanesulfonate 
• 486-25-9 9-fluorenone 
• 952128-76-6 [(pentamethylcyclopentadienide)₂Co][OTf] 
• 64-18-6 formic acid 
• 201230-82-2 carbon monoxide 
• 1333-74-0 hydrogen 

Relevant academic research and scientific papers

Dissolution of oligo(tetrafluoroethylene) and preparation of poly(tetrafluoroethylene)-based composites by using fluorinated ionic liquids

Fluorophilic ionic liquids (ILs) showing enhanced compatibility with poly(tetrafluoroethylene) (PTFE) have been newly synthesised. The as-designed ILs contributed both to the dissolution of PTFE oligomers and to the preparation of composites with PTFE with no fear of bleed-out of the ILs.

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.

Rapid, High-Yield Fructose Dehydration to 5-Hydroxymethylfurfural in Mixtures of Water and the Noncoordinating Ionic Liquid [bmim][OTf]

The noncoordinating ionic liquid [bmim][OTf] (bmim=1-butyl-3-methylimidazolium) is an effective and versatile solvent for the high-yield dehydration of fructose to the platform chemical 5-hydroxymethylfurfural (HMF) over short reaction times. In contrast to prior studies in which low yields were obtained for this transformation in ionic liquids (ILs) with noncoordinating anions, this contribution reveals that the water content is an essential parameter for an efficient reaction in ILs. Achieving the optimum amount of water can increase the yield dramatically by regulating the acidity of the catalyst and partially suppressing the side reaction caused by self-condensation of HMF. Using acid catalysis in [bmim][OTf] with 3.5 % water content, yields above 80 % can be achieved at 100 °C in only 10 min, even at high (14 %) fructose loading. These results also suggest that [bmim][OTf] represents a superior medium for solvent extraction of HMF compared to halide-based ILs, allowing the option of isolation or further valorization of the HMF formed.

The conductivity of imidazolium-based ionic liquids from (248 to 468) K. B. variation of the anion

The effect of the anion, namely dicyanamide, hexafluorophosphate, trifluoroacetate, or trifluoromethanesulfonate, on the conductivity (κ) of 1-N-butyl-3-N-methylimidazolium-based room-temperature ionic liquids (RTILs) was studied over the temperature range (248 to 468) K. The uncertainty in κ was estimated to be less than 0.5 %. The conductivity values obtained are well-described by the Vogel-Fulcher-Tammann equation. Additionally, densities (ρ) and the corresponding molar conductivities (Λ) are reported for the temperature range (278 to 338) K. The data for Λ and the associated viscosities (η) were found to fit fractional forms of the Walden relationship.

[{Fe(CO)3}4{SnI}6I4] 2-: The first bimetallic adamantane-like cluster

Show some metal: The first bimetallic adamantane-like cluster, [{Fe(CO)3}4{SnI}6I4]2- (see structure), was prepared by an ionic-liquid-based synthesis. The valence states of iron and tin were verified

Eu3 + as a dual probe for the determination of IL anion donor power: A combined luminescence spectroscopic and electrochemical approach

This work is aimed at giving proof that Eu(Tf2N)3 (Tf2N = bis(trifluoromethanesulfonyl)amide) can act as both an optical and electrochemical probe for the determination of the Lewis acidity of an ionic liquid anion. For that reason the luminescence spectra and cyclic voltammograms of dilute solutions of Eu(Tf2N)3 in various ionic liquids were investigated. The Eu2 +/3 + redox potential in the investigated ILs can be related to the Lewis basicity of the IL anion. The IL cation had little influence. The lower the determined halfwave potential, the higher the IL anion basicity. The obtained ranking can be confirmed by luminescence spectroscopy where a bathochromic shift of the 5D 0 → 7F4 transition indicates a stronger Lewis basicity of the IL anion.

Theoretical and experimental comparative study of nonlinear properties of imidazolium cation based ionic liquids

This work describes the experimental and theoretical investigation of the nonlinear optical properties of the imidazolium cation based ionic liquids and the corresponding thermo-optical parameters. The experimental results of nonlinear optical properties, such as nonlinear refractive index and thermo-optical properties are determined by Z-scan and EZ-scan techniques with a femtosecond laser source. Theoretical simulations of linear and nonlinear optical properties performed by density functional theory (DFT) are discussed in terms of polarizabilities and hyperpolarizabilities. A correlation between the theoretical and experimental results is presented, where the variation of the experimental signals of each ionic liquid can be compared with their calculated nonlinear optical properties.

Physical and electrochemical properties of ionic liquids 1-ethyl-3-methylimidazolium tetrafluoroborate, 1-butyl-3-methylimidazolium trifluoromethanesulfonate and 1-butyl-1-methylpyrrolidinium bis(trifluoromethylsulfonyl)imide

The ionic liquids 1-ethyl-3-methylimidazolium tetrafluoroborate 1-butyl-3-methylimidazolium trifluoromethanesulfonate and 1-butyl-1- methylpyrrolidinium bis(trifluoromethylsulfonyl)imide were prepared and several of their properties including viscosities, thermal stability, surface tension, refractive index, pH and density were investigated as a function of temperature. The coefficients of thermal expansion of the ionic liquids were also calculated from the experimental values of the density at various temperatures. The electrochemical stability of the ionic liquids, as electrolytes for voltammetric aspects, was studied at glassy carbon electrode. The results revealed a wide voltage range of the electrochemical window, which allowed studies on compounds such as furaldehydes.

Determination of halide impurities in ionic liquids by total reflection X-ray fluorescence spectrometry

The determination and quantification of halide impurities in ionic liquids is highly important because halide ions can significantly influence the chemical and physical properties of ionic liquids. The use of impure ionic liquids in fundamental studies on solvent extraction or catalytic reactions can lead to incorrect experimental data. The detection of halide ions in solution by total reflection X-ray fluorescence (TXRF) has been problematic because volatile hydrogen halide (HX) compounds are formed when the sample is mixed with the acidic metal standard solution. The loss of HX during the drying step of the sample preparation procedure gives imprecise and inaccurate results. A new method based on an alkaline copper standard Cu(NH3) 4(NO3)2 is presented for the determination of chloride, bromide, and iodide impurities in ionic liquids. The 1-butyl-3-methylimidazolium ([C4mim]) ionic liquids with the anions acetate ([C4mim][OAc]), nitrate ([C4mim][NO3]), trifluoromethanesulfonate ([C4mim][OTf]), and bis(trifluoromethylsulfonyl)imide ([C4mim][Tf2N]) were synthesized via a halide-free route and contaminated on purpose with known amounts of [C4mim]Cl, [C4mim]Br, [C4mim]I, or potassium halide salts in order to validate the new method and standard.

Densities and viscosities of 1-butyl-3-methylimidazolium trifluoromethanesulfonate + H2O binary mixtures at T = (303.15 to 343.15) K

Densities and viscosities for the binary mixtures of H2O (1) + 1-butyl-3-methylimidazolium trifluoromethanesulfonate ([BMIM][CF 3SO3]) (2) were measured over the entire mole fraction range from (303.15 to 343.15) K at atmospheric pressure. Excess molar volumes and viscosity deviations as a function of mole fraction average were derived, and the results were fitted to the Redlich-Kister equation using a multiparametric nonlinear regression method. Estimated coefficients of the Redlich-Kister equation and standard error calculated from the Redlich-Kister equation to the experimental data are also presented. The results show that the densities and viscosities are dependent on water content and temperature.