174899-66-2

Basic information

• Product Name: 1-Butyl-3-methylimidazolium trifluoromethansulfonate
• Synonyms: Basionics? VS 12;3-butyl-1-methyl-1H-Imidazolium 1,1,1-trifluoromethanesulfonate;1-N-BUTYL-3-METHYLIMIDAZOLIUM TRIFLUOROMETHANESULFONATE;1-BUTYL-3-METHYLIMIDAZOLIUM TRIFLUOROMETHANESULFONATE;1-BUTYL-3-METHYL-IMIDAZOLIUM TRIFLUOROMETHANSULFONATE;1-BUTYL-3-METHYLIMIDAZOLIUM TRIFLUOROMETHYLSULFONATE;1-BUTYL-3-METHYL-IMIDAZOLIUM TRIFLUORMETHANSULFONATE;1-BUTYL-3-ETHYLIMIDAZOLIUM TRIFLUOROMETHANESULFONATE
• CAS NO: 174899-66-2
• Molecular Formula: CF₃O₃S*C₈H₁₅N₂
• Molecular Weight: 288.29
• EINECS: 200-145-6
• Product Categories: Specialty Synthesis;Imidazolium Compounds;Imidazolium Salts (Ionic Liquids);Ionic Liquids;Synthetic Organic Chemistry;Chemical Synthesis;Imidazolium
• Mol File: 174899-66-2.mol
• Article Data: 44

Chemical Properties

• Melting Point: 16°C
• Flash Point: >100°C
• Appearance: /
• Density: 1.292 g/mL at 20 °C(lit.)
• Refractive Index: 1.434
• Storage Temp.: Store below +30°C.
• Sensitive: Hygroscopic
• CAS DataBase Reference: 1-Butyl-3-methylimidazolium trifluoromethansulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Butyl-3-methylimidazolium trifluoromethansulfonate(174899-66-2)
• EPA Substance Registry System: 1-Butyl-3-methylimidazolium trifluoromethansulfonate(174899-66-2)

Safety Data

• Hazard Codes: Xn,Xi,N,T
• Statements: 36/37/38-21/22-51/53-36/38-25-23/24/25
• Safety Statements: 36/37/39-26-61-45-36-22
• RIDADR: 3265
• WGK Germany: 3
• Hazardous Substances Data: 174899-66-2(Hazardous Substances Data)

Usage

Description

1-Butyl-3-methylimidazolium trifluoromethansulfonate, also known as [bmim][OTf], is a versatile ionic liquid that is clear pale yellow to yellow in color. It is widely used in synthetic chemistry due to its unique properties and applications.

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 
• 1493-13-6 trifluorormethanesulfonic acid 
• 342789-81-5 1-n-butyl-3-methylimidazolium methanesulfonate 
• 2926-30-9 sodium triflate 
• 616-47-7 1-methyl-1H-imidazole 
• 71-36-3 butan-1-ol 
• 109-65-9 1-bromo-butane 
• 2926-27-4 potassium trifluoromethansulfonate 
• 85100-77-2 1-n-butyl-3-methylimidazolim bromide 
• 1912-32-9 n-butyl methanesulfonate 
• 77-78-1 dimethyl sulfate 

Downstream Products

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

Relevant articles and documents

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.

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.

[{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

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.

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.

An environmentally benign attribute for the expeditious synthesis of quinoxaline and its derivatives

A simple, efficient, and environmentally friendly ionic liquid mediated protocol for the synthesis of quinoxaline derivatives using carbonyl substrate and phenylenediamines has been described. A range of ionic liquids were synthesized, characterized via IR, 1H and 13C NMR and used as a solvent as well as catalyst for above protocol. The catalytic activities of ILs were evaluated and the relationship between the catalytic activity and acidity was discussed. It was also found that among the all ILs, [Bmim]CF3SO3 was the most effective, eco-friendly and less expensive solvent and catalyst for the above etiquette. This method is of significant value due to the eco-friendly nature of ionic liquid and non usage of separate catalyst to drive the reaction forward. The protocol proves to be efficient and environmentally benign in terms of good to excellent yields, low reaction times, simple work-up, ease of recovery, and reusability of ionic liquid for six times.

The effect of varying the anion of an ionic liquid on the solvent effects on a nucleophilic aromatic substitution reaction

A variety of ionic liquids, each containing the same cation but a different anion, were examined as solvents for a nucleophilic aromatic substitution reaction. Varying the proportion of ionic liquid was found to increase the rate constant as the mole fraction of ionic liquid increased demonstrating that the reaction outcome could be controlled through varying the ionic liquid. The solvent effects were correlated with the hydrogen bond accepting ability (β) of the ionic liquid anion allowing for qualitative prediction of the effect of changing this component of the solute. To determine the microscopic origins of the solvent effects, activation parameters were determined through temperature-dependent kinetic analyses and shown to be consistent with previous studies. With the knowledge of the microscopic interactions in solution, an ionic liquid was rationally chosen to maximise rate enhancement demonstrating that an ionic solvent can be selected to control reaction outcome for this reaction type.