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174899-82-2 Usage

Description

It is a typical ionic liquid usually used as the solvent in the organic synthesis and chemical industry. For example, this chemical can act as the solvent for dissolving CO2 gas.1 This substance may also function as the solvent for dissolving the electroactive oxygen, thus allowing for the study of electrochemical reduction of oxygen by cyclic voltammetry at a gold microdisk electrode.2 Moreover, determination of ammonia based on electro-oxidation of hydroquinone has been carried out by using this compound as the solvent.3 Besides, nanoparticles of ZnO with the wurtzite structure have been synthesized via a microwave through the decomposition of zinc acetate dihydrate in 1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide as a solvent.4

Referrence

Schilderman, A. M.; Raeissi, S.; Peters, C. J., Solubility of carbon dioxide in the ionic liquid 1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide. Fluid Phase Equilib. 2007, 260, 19-22. Buzzeo, M. C.; Klymenko, O. V.; Wadhawan, J. D.; Hardacre, C.; Seddon, K. R.; Compton, R. G., Voltammetry of oxygen in the room-temperature ionic liquids 1-ethyl-3-methylimidazolium bis((trifluoromethyl)sulfonyl)imide and hexyltriethylammonium bis((trifluoromethyl)sulfonyl)imide: One-electron reduction to form superoxide. Steady-state and transient behavior in the same cyclic voltammogram resulting from widely different diffusion coefficients of oxygen and superoxide. J. Phys. Chem. A 2003, 107, 8872-8878. Giovanelli, D.; Buzzeo, M. C.; Lawrence, N. S.; Hardacre, C.; Seddon, K. R.; Compton, R. G., Determination of ammonia based on the electro-oxidation of hydroquinone in dimethylformamide or in the room temperature ionic liquid, 1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide. Talanta 2004, 62, 904-911. Goharshadi, E. K.; Ding, Y.; Nancarrow, P., Green synthesis of ZnO nanoparticles in a room-temperature ionic liquid 1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide. J. Phys. Chem. Solids 2008, 69, 2057-2060.

Conductivity

6.63 mS/cm

Chemical Properties

Clear colorless liquid

Uses

1-Ethyl-3-methylimidazolium bis(Trifluoromethylsulfonyl)imide is an ionic liquid; used in method for regulating thermal response temperature of ionic liquid gel and thermal response ionic liquid gel.

General Description

1-Ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide [EMIM][N(Tf)2] is a room temperature ionic liquid (RTIL). ([EMIM][N(Tf)2]) as a non-aqueous solvent, is advantageous over traditional aprotic polar organic solvents in electrochemical investigation of electroactive species since it has low vapor pressure, high thermal stability, good conductivity and a wide electrochemical window. [EMIM][N(Tf)2] shows good solubility in CO2.

Check Digit Verification of cas no

The CAS Registry Mumber 174899-82-2 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,7,4,8,9 and 9 respectively; the second part has 2 digits, 8 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 174899-82:
(8*1)+(7*7)+(6*4)+(5*8)+(4*9)+(3*9)+(2*8)+(1*2)=202
202 % 10 = 2
So 174899-82-2 is a valid CAS Registry Number.
InChI:InChI=1/C6H11N2.C2F6NO4S2/c1-3-8-5-4-7(2)6-8;3-1(4,5)14(10,11)9-15(12,13)2(6,7)8/h4-6H,3H2,1-2H3;/q+1;-1

174899-82-2 Well-known Company Product Price

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  • TCI America

  • (E0599)  1-Ethyl-3-methylimidazolium Bis(trifluoromethanesulfonyl)imide  >98.0%(HPLC)(T)

  • 174899-82-2

  • 5g

  • 815.00CNY

  • Detail
  • TCI America

  • (E0599)  1-Ethyl-3-methylimidazolium Bis(trifluoromethanesulfonyl)imide  >98.0%(HPLC)(T)

  • 174899-82-2

  • 25g

  • 2,940.00CNY

  • Detail
  • Sigma-Aldrich

  • (11291)  1-Ethyl-3-methylimidazoliumbis(trifluoromethylsulfonyl)imide  ≥97.0% (NMR)

  • 174899-82-2

  • 11291-1G-F

  • 1,880.19CNY

  • Detail
  • Sigma-Aldrich

  • (11291)  1-Ethyl-3-methylimidazoliumbis(trifluoromethylsulfonyl)imide  ≥97.0% (NMR)

  • 174899-82-2

  • 11291-5G-F

  • 7,179.12CNY

  • Detail
  • Aldrich

  • (711691)  1-Ethyl-3-methylimidazoliumbis(trifluoromethylsulfonyl)imide  ≥98% (HPLC)

  • 174899-82-2

  • 711691-100G

  • 2,300.22CNY

  • Detail
  • Aldrich

  • (711691)  1-Ethyl-3-methylimidazoliumbis(trifluoromethylsulfonyl)imide  ≥98% (HPLC)

  • 174899-82-2

  • 711691-1KG

  • 13,712.40CNY

  • Detail

174899-82-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-Ethyl-3-Methylimidazolium Bis(Trifluoromethylsulfonyl)Imide

1.2 Other means of identification

Product number -
Other names 1-Ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

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Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:174899-82-2 SDS

174899-82-2Relevant articles and documents

Improved solubilization of pyromellitic dianhydride and 4,4′-oxydianiline in ionic liquid by the addition of zwitterion and their polycondensation

Tamada, Masahiro,Hayashi, Takahiro,Ohno, Hiroyuki

, p. 1553 - 1557 (2007)

Three different ionic liquids were prepared and examined as solvents for polyimide synthesis. The solubility of 4,4′-oxydianiline and pyromellitic dianhydride as starting materials in ionic liquids was first evaluated, and then their polycondensation was carried out. Although these starting materials were hardly soluble in 1-benzyl-3-methylimidazolium bis(trifluoromethane sulfonyl)imide (3), addition of imidazolium type zwitterion, 1-(1-butyl-3-imidazolio)butane-4-sulfonate (ZI), certainly improved their solubility. When 3 containing 40 mol % ZI was used, nothing was phase separated from this mixed solution containing both starting materials after cooling down to room temperature. After preparing prepolymer in 3 containing 40 mol % of ZI at room temperature, polycondensation was carried out in the same solution at 100, 200, and then 300 °C for every 1 h to obtain polyimide. An inherent viscosity of the obtained polyimide (0.05 g in 10 ml concentrated sulfuric acid) was 1.3 dL g-1, higher than that prepared in only 3 (0.9 dL g-1). The higher average molecular weight of the polyimide was attributed to the improved solubility of the starting materials by the addition of ZI that enabled the preparation of the prepolymer, poly(amide acid), without heating before imidation.

Novel viologen derivatives for electrochromic ion gels showing a green-colored state with improved stability

Oh, Hwan,Seo, Dong Gyu,Yun, Tae Yong,Lee, Seong Been,Moon, Hong Chul

, p. 490 - 495 (2017)

We successfully synthesized a novel viologen derivative (1,1′-bis(3-fluoro-4-(trifluoromethyl)phenyl)-4,4′-bipyridinium bis(trifluoromethylsulfonyl)imide, TFMFPhV(TFSI)2) exhibiting a green-colored state. We selected cyanophenyl viologen (CNPhV2+), a conventional electrochromic (EC) chromophore with a green color indication, to compare EC performance. Ion gels consisting of poly(vinylidene fluoride-co-hexafluoropropylene) (PVDF-co-HFP) and 1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide ([EMI][TFSI]) were employed as a solid-state electrolyte for EC devices (ECDs). In comparison to CNPhV2+-containing devices, the ECDs with TFMFPhV2+ showed higher transmittance contrast, larger coloration efficiency, faster coloration and bleaching responses, and better coloration/bleaching operational stability. Cyclic voltammetry revealed that the more stable redox behavior of TFMFPhV2+ is the origin of the outstanding ECD performance.

Structural diversity in hybrid vanadium(iv) oxyfluorides based on a common building block

Aidoudi, Farida H.,Black, Cameron,Arachchige, Kasun S. Athukorala,Slawin, Alexandra M. Z.,Morris, Russell E.,Lightfoot, Philip

, p. 568 - 575 (2014)

There are only limited reports on vanadium(iv) oxyfluorides (VOFs) with extended crystal structures. Here we expand and enrich the list of existing VOFs with a series of 14 new materials "VOF-n (n = 1-14)" prepared using ionothermal and solvothermal synthesis methods. All of these materials arise from the condensation of a dimeric structural motif. These VOFs can be classified into three groups depending on their key structural features; layer structures: VOF-1 "[HN2C7H6][V 2O2F5]", VOF-2 "[HN2C 4H4][V2O2F5]", VOF-3 "[HN2C3H4][V2O 2F5]" and VOF-4 "V2(N 2C4H4)O2F4", ladder like structures: VOF-5 "[NH4(HN2C3H 4)][V2O2F6]", VOF-6 "[K(HN2C3H4)][V2O 2F6]", VOF-7 "[HNH2CH 2CH3][VOF3]", VOF-8 "[HN 2C7H6][VOF3]", VOF-9 "[H2N2C4H6][V2O 2F6]", VOF-10 "β-RbVOF3", VOF-11"α-KVOF3", VOF-12 "β-KVOF 3", VOF-13 "[H2(NH2) 2(CH2)2][V2O2F 6]", and a chain structure: VOF-14 "[H2N 2C6H12][V2O2F 7]". The crystal structures of VOF-n are presented, and their synthetic and structural relationships are discussed.

Coordination and extraction of mercury(ii) with an ionic liquid-based thione extractant

Lu, Wenjuan,Barber, Patrick S.,Kelley, Steven P.,Rogers, Robin D.

, p. 12908 - 12916 (2013)

A neutral thione extractant, 1,3-diethylimidazole-2-thione (C 2C2ImT), was prepared from an ionic liquid (IL), 1,3-diethylimidazolium acetate, and used within a hydrophobic ionic liquid, 1-ethyl-3-methylimidazolium bis(trifluoromethane)sulfonamide ([C 2mim][NTf2]), to extract Hg(ii) from aqueous solutions of HgCl2 or Hg(OAc)2. Investigations of the extraction mechanism, spectroscopic analyses of the extracted species, and crystallographic studies of the interactions of C2C2ImT with Hg(ii) are reported, including the first structurally characterized Hg-NTf2 coordination compound, Hg(C2C2ImT)2(NTf 2)2. Coordination complexes of the thione ligand with Hg(ii) show variability in coordination numbers and geometries with stoichiometry, suggesting that the extraction mechanism is dependent on the speciation of mercury in aqueous solution. HgCl2 can form neutral, extractable complexes with the thione in aqueous solution. Hg(OAc)2 dissociates on dissolution in water and Hg(ii) is extracted through a cation exchange mechanism involving [Hg(C2C2ImT) 2]2+ ions. The precipitation of neutral mercury complexes from the IL following the extraction of excess mercury suggests a simple and unusual way to recycle the IL.

Ionic liquids based on (fluorosulfonyl)(pentafluoroethanesulfonyl)imide with various oniums

Liu, Kai,Zhou, Yi-Xuan,Han, Hong-Bo,Zhou, Si-Si,Feng, Wen-Fang,Nie, Jin,Li, Hong,Huang, Xue-Jie,Armand, Michel,Zhou, Zhi-Bin

, p. 7145 - 7151 (2010)

New hydrophobic ionic liquids based on (fluorosulfonyl) (pentafluoroethanesulfonyl)imide ([(FSO2)(C2F 5SO2)N]-, FPFSI-) anion with various oniums, including imidazolium, tetraalkyl ammonium, pyrrolidinium, and piperidinium, were prepared and characterized. Their physicochemical and electrochemical properties, including phase transitions, thermal stability, viscosity, density, specific conductivity and electrochemical windows, were extensively characterized, and were comparatively studied with the corresponding ionic liquids containing the isomeric but symmetric TFSI- ([(CF 3SO2)2N]-) anion. These new FPFSI--based ionic liquids display low melting points, low viscosities, good thermal stability, and wide electrochemical windows allowing Li deposition/dissolution. All these desired properties suggest they are potential electrolyte materials for Li (or Li-ion) batteries.

Coordination of terpyridine to Li+ in two different ionic liquids

Pokorny, Klaus,Schmeisser, Matthias,Hampel, Frank,Zahl, Achim,Puchta, Ralph,Van Eldik, Rudi

, p. 13167 - 13178 (2013)

On the basis of 7Li NMR experiments, the complex-formation reaction between Li+ and the tridentate N-donor ligand terpyridine was studied in the ionic liquids [emim][NTf2] and [emim][ClO 4] as solvents. For both ionic liquids, the NMR data implicate the formation of [Li(terpy)2]+. Density functional theory calculations show that partial coordination of terpyridine involving the coordination of a solvent anion can be excluded. In contrast to the studies in solution, X-ray diffraction measurements led to completely different results. In the case of [emim][NTf2], the polymeric lithium species [Li(terpy)(NTf2)]n was found to control the stacking of this complex, whereas crystals grown from [emim][ClO4] exhibit the discrete dimeric species [Li(terpy)(ClO4)]2. However, both structures indicate that each lithium ion is formally coordinated by one terpy molecule and one solvent anion in the solid state, suggesting that charge neutralization and π stacking mainly control the crystallization process.

Solvent extraction of Sr2+ and Cs+ based on room-temperature ionic liquids containing monoaza-substituted crown ethers

Luo, Huimin,Dai, Sheng,Bonnesen, Peter V.

, p. 2773 - 2779 (2004)

A series of N-alkyl aza-18-crown-6 ethers were synthesized and characterized by NMR spectroscopy and mass spectrometry. These monoaza-substituted crown ethers in ionic liquids were investigated as recyclable extractants for separation of Sr2+ and Cs+ from aqueous solutions. The pH-sensitive complexation capability of these ligands allows for a facile stripping process to be developed so that both macrocyclic ligands and ionic liquids can be reused. The extraction efficiencies and selectivities of these monoaza-substituted crown ethers for Na+, K+, Cs+, and Sr2+ were studied in comparison to those of dicyclohexano-18-crown-6 under the same conditions. The extraction selectivity order for dicyclohexano-18-crown-6 in the ionic liquids investigated here was K+ ? Sr2+ > Cs + > Na+. The extraction selectivity order for N-alkyl aza-18-crown-6, in which the alkyl group is varied systematically from ethyl to n-dodecyl, was Sr2+ ? K+ > Cs+ > Na+ in 1-ethyl-3-methylimidazolium bis[(trifluoromethyl)sulfonyl]amide and 1-butyl-3-methylimidazolium bis[(trifiuoromethyl)suffonyl]amide and K+ > Sr2+ > Cs+ > Na+ in 1-hexyl-3-methylimidazolium bis[(trifluoromethyl)sulfonyl] amide and 1-octyl-3-methylimidazolium bis[(trifluoromethyl)sulfonyl]amide. The strong dependence of selectivity on the type of ionic liquid indicates an important role played by solvation in solvent extraction processes based on ionic liquids. The optimization of macrocyclic ligands and ionic liquids led to an extraction system that is highly selective toward Sr2+.

Directed Phase Transfer of an FeII4L4 Cage and Encapsulated Cargo

Grommet, Angela B.,Nitschke, Jonathan R.

, p. 2176 - 2179 (2017)

Supramolecular capsules can now be prepared with a wide range of volumes and geometries. Consequently, many of these capsules encapsulate guests selectively by size and shape, an important design feature for separations. To successfully address practical separations problems, however, a guest cannot simply be isolated from its environment; the molecular cargo must be removed to a separate physical space. Here we demonstrate that an FeII4L4 coordination cage 1 can transport a cargo spontaneously and quantitatively from water across a phase boundary and into an ionic liquid layer. This process is triggered by an anion exchange from 1[SO4] to 1[BF4]. Upon undergoing a second anion exchange, from 1[BF4] to 1[SO4], the cage, together with its encapsulated guest, can then be manipulated back into a water layer. Furthermore, we demonstrate the selective phase transfer of cationic cages to separate a mixture of two cages and their respective cargoes. We envisage that supramolecular technologies based upon these concepts could ultimately be employed to carry out separations of industrially relevant compounds.

Distillable ionic liquids: Reversible amide OAlkylation

Chen, Zheng-Jian,Xi, Hong-Wei,Lim, Kok Hwa,Lee, Jong-Min

, (2013)

Put it in reverse: The recycling of ionic liquids (ILs) by distillation of the regenerated volatile precursors was demonstrated to be feasible by using low-cost amide-cation-derived aprotic ionic liquids prepared from reversible Oalkylation. The low visco

Acute toxicity of cu-mof nanoparticles (Nanohkust-1) towards embryos and adult zebrafish

Abramenko, Natalia,Deyko, Gregory,Abkhalimov, Evgeny,Isaeva, Vera,Pelgunova, Lyubov,Krysanov, Eugeny,Kustov, Leonid

, (2021)

Metal-organic frameworks (MOFs) demonstrate unique properties, which are prospective for drug delivery, catalysis, and gas separation, but their biomedical applications might be limited due to their obscure interactions with the environment and humans. It is important to understand their toxic effect on nature before their wide practical application. In this study, HKUST-1 nanoparticles (Cu-nanoMOF, Cu3 (btc)2, btc = benzene-1,3,5-tricarboxylate) were synthesized by the microwave (MW)-assisted ionothermal method and characterized by X-ray powder diffraction (XRD) and transmission electron microscopy (TEM) techniques. The embryotoxicity and acute toxicity of HKUST-1 towards embryos and adult zebrafish were investigated. To gain a better understanding of the effects of Cu-MOF particles towards Danio rerio (D. rerio) embryos were exposed to HKUST-1 nanoparticles (NPs) and Cu2+ ions (CuSO4 ). Cu2+ ions showed a higher toxic effect towards fish compared with Cu-MOF NPs for D. rerio. Both forms of fish were sensitive to the presence of HKUST-1 NPs. Estimated LC50 values were 2.132 mg/L and 1.500 mg/L for zebrafish embryos and adults, respectively. During 96 h of exposure, the release of copper ions in a stock solution and accumulation of copper after 96 h were measured in the internal organs of adult fishes. Uptake examination of the major internal organs did not show any concentration dependency. An increase in the number of copper ions in the test medium was found on the first day of exposure. Toxicity was largely restricted to copper release from HKUST-1 nanomaterials structure into solution.

Excess Molar Volume and Viscosity Deviation of [C2mim][NTf2]/[C4mim][NTf2] + DMC/DEC

Liu, Qingshan,Zhao, Liwei,Zheng, Qige,Mou, Lin,Zhang, Pengfei

, p. 4484 - 4496 (2018)

Two hydrophobic ionic liquids (ILs) 1-alkyl-3-methylimidazolium bis[(trifluoromethyl)sulfonyl]imide ([C2mim][NTf2] and [C4mim][NTf2]) were synthesized. The binary mixtures of the two ILs were prepared with dimethyl carbonate (DMC) or diethyl carbonate (DEC) over the entire mole fraction range, respectively. The density and viscosity of the binary mixtures were determined by an automated DMA 5000 M and a Lovis 2000 ME Anton Paar Rotational Stabinger Viscometer at temperatures ranging from 288.15 to 328.15 K. The uncertainties of the density and viscosity are ur(δ) = 0.00120 and ur(δ) = 0.01. The excess molar volumes and viscosity deviations were calculated for the four binary mixtures by the measurement values. The effects of the extension of the alkyl chain of the cation and anion on the above properties are discussed. The effects of the methyl introduction on the cation was also discussed with the literature. The excess molar volumes and viscosity deviations were fitted versus mole fraction according to the Redlich-Kister equation. The thermal expansion coefficients of the systems were calculated according to the density values.

The effect of light penetration depth on the LCST phase behavior of a thermo- and photoresponsive statistical copolymer in an ionic liquid

Hall, Cecilia C.,Rivera, Cecelia A.,Lodge, Timothy P.

, p. 281 - 287 (2019)

A reflection cloud point technique allows for rapid screening of light-dependent phase separation temperatures of thermo- and photoresponsive polymer/ionic liquid solutions as a function of sample thickness, molecular weight, and copolymer composition. We systematically investigate the lower critical solution temperature (LCST) phase behavior of poly(benzyl methacrylate-stat-(4-phenylazophenyl methacrylate)). Under UV light, the photoresponsive azobenzene-based repeat unit becomes more polar as the cis form dominates, increasing its solubility in the ionic liquids 1-ethyl-3-methyl imidazolium and 1-butyl-3-methyl imidazolium bis(trifluoromethanesulfonyl)imide. This light-dependent polarity change leads to two phase separation temperatures, depending on the illumination wavelength. Under visible light, which drives the azobenzene moiety into the trans ground state, the LCST shows no sample thickness dependence. Under UV light, however, sample thickness plays a significant role. Samples of around 1 mm thickness show no apparent difference under UV and visible light, whereas thinner samples show an increasing difference between the phase separation temperatures with decreasing sample thickness. Neither phase separation temperature exhibits a significant dependence on molecular weight. Increasing the photoresponsive monomer content did not lead to an increase in the difference between the phase separation temperatures at fixed thickness, due to a concomitant increase in UV light absorbed at the sample surface.

Preparation method of dialkylimidazole bis(trifluoromethylsulfonyl)imide salt

-

Paragraph 0064; 0066, (2020/03/25)

The invention discloses a preparation method of a dialkylimidazole bis(trifluoromethylsulfonyl)imide salt. The method comprises the following steps: 1, reacting alkylimidazole with sulfate in an organic solvent, and layering the obtained solution to obtain a crude dialkylimidazole sulfate product; 2, washing the crude dialkylimidazole sulfate product, carrying out reduced pressure distillation, and drying the obtained product to obtain dialkylimidazole sulfate; 3, reacting the dialkylimidazole sulfate with a bis(trifluoromethylsulfonyl)imide metal salt, and layering the obtained solution to obtain a crude dialkylimidazole bis(trifluoromethylsulfonyl)imide salt product; and 4, washing the crude dialkylimidazole bis(trifluoromethylsulfonyl)imide salt product, carrying out reduced pressure distillation, and drying the obtained product to obtain the target product dialkylimidazole bis(trifluoromethylsulfonyl)imide salt. The method has the advantages of mild reaction conditions, simple operation steps, realization of high yield, high purity and low halogen ion content of the prepared product, and suitableness for promotion and application.

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