143314-16-3

Basic information

• Product Name: 1-Ethyl-3-methylimidazolium tetrafluoroborate
• Synonyms: EMIMBF4;1-ETHYL-3-METHYL-1 H-IMIDAZOLIUM TETRAFLUOROBORATE;1-ETHYL-3-METHYLIMIDAZOLIUM TETRAFLUOROBORATE;EMIMBF4;1-Ethyl-3-methylimidazolium tetrafluorob;Ethylmethylimidazoliumtetrafluoroborate;formoltensalt;1-ETHYL-3-METHYLIMIDAZOLIUM TETRAFLUOROBORATE 97+%
• CAS NO: 143314-16-3
• Molecular Formula: BF₄*C₆H₁₁N₂
• Molecular Weight: 197.97
• EINECS: -0
• Product Categories: B (Classes of Boron Compounds);Imidazolium Compounds;Imidazolium Salts (Ionic Liquids);Ionic Liquids;Synthetic Organic Chemistry;Tetrafluoroborates;Ionic liquid
• Mol File: 143314-16-3.mol
• Article Data: 41

Chemical Properties

• Melting Point: 15 °C(lit.)
• Boiling Point: >350 °C(lit.)
• Flash Point: >230 °F
• Appearance: /liquid
• Density: 1.294 g/mL at 25 °C(lit.)
• Vapor Pressure: 0-0Pa at 20-25℃
• Refractive Index: n20/D 1.413(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• Sensitive: Hygroscopic
• CAS DataBase Reference: 1-Ethyl-3-methylimidazolium tetrafluoroborate(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Ethyl-3-methylimidazolium tetrafluoroborate(143314-16-3)
• EPA Substance Registry System: 1-Ethyl-3-methylimidazolium tetrafluoroborate(143314-16-3)

Safety Data

• Hazard Codes: Xn,N
• Statements: 36/38-51/53-22-24/25-23
• Safety Statements: 23-24/25-61
• RIDADR: UN3082 9/PG 3
• WGK Germany: 3
• F: 3-10
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 143314-16-3(Hazardous Substances Data)

Usage

Conductivity

14.1 mS/cm (25 °C)

Chemical Properties

Light yellow liquid

Uses

Different sources of media describe the Uses of 143314-16-3 differently. You can refer to the following data:
1. 1-Ethyl-3-methylimidazolium tetrafluoroborate is an ionic liquid used in the recycling of osmium in the dihydroxylation of olefins with osmium(VIII)? oxide. It is a stable liquid electrolyte used in the capillary electrophoretic method for resolving phenolic compounds present in grape seed extract. It also acts as a good solvent for a wide range of both organic and inorganic compounds.
2. 1-Ethyl-3-methylimidazolium tetrafluoroborate is a room temperature ionic liquid widely used as an electrolyte in electrochemical studies. Its diffusion coefficient, 13C spin-lattice relaxation times, and nuclear Overhauser enhancements have been analyzed using NMR techniques to study its hydrogen bonding. Some of its fundamental physical and chemical properties such as density, viscosity, thermal stability, surface tension, refractive index and pH have been studied over a wide range of temperature.
3. The enzymatic resolution of homophenylalanine ester to form enantiomeric homophenylalanine can be performed using 1-ethyl-3-methylimidazolium tetrafluoroborate as a reaction medium.

General Description

1-Ethyl-3-methylimidazolium tetrafluoroborate is an air and water stable, room temperature ionic liquid (RTIL). It can be prepared by reacting 1-ethyl-3-methylimidazolium bromide with tetrafluoroboric acid.

InChI:InChI=1/C6H11N2.BF4/c1-3-8-5-4-7(2)6-8;2-1(3,4)5/h4-6H,3H2,1-2H3;/q+1;-1

Upstream product

• 616-47-7 1-methyl-1H-imidazole 
• 74-96-4 ethyl bromide 
• 78-10-4 tetraethoxy orthosilicate 
• 13755-29-8 sodium tetrafluoroborate 
• 65039-08-9 3-ethyl-1-methyl-1H-imidazol-3-ium bromide 
• 14104-20-2 silver tetrafluoroborate 
• 65039-09-0 1-ethyl-3-methyl-1H-imidazol-3-ium chloride 
• 7098-07-9 N-Ethylimidazole 
• 14075-53-7 potassium tetrafluoroborate 
• 250358-46-4 1-ethyl-3-methylimidazolium hydroxide 
• 35935-34-3 1-ethyl-3-methylimidazolium iodide 
• 420-37-1 trimethoxonium tetrafluoroborate 
• 368-39-8 triethyloxonium fluoroborate 
• 64-17-5 ethanol 

Downstream Products

• 377739-43-0 1-ethyl-3-methyl-imidazolium tris(pentafluoroethyl)trifluorophosphate 
• 7637-07-2 boron trifluoride 
• 60-29-7 diethyl ether 
• 353-36-6 1-fluoroethane 
• 1447933-86-9 C₁₆H₂₃N₄O₂⁽¹⁺⁾*BF₄^(1-) 

Relevant articles and documents

Physical and electrochemical properties of 1-alkyl-3-methylimidazolium tetrafluoroborate for electrolyte

Three kinds of ionic liquids, 1-alkyl-3-methylimidazolium tetrafluoroborate (n = 2-4), were prepared and fundamental properties of ionic liquids and those mixed with industrially used organic solvents (PC, GBL and AN) were investigated compared to solid salts, TEMABF4. It was found that degree of ionization of the ionic liquids were almost same as that of TEMABF4 from the conductivity measurement in diluted system of PC. The ionic liquids and the organic solvents intermingle with each other. Some enhancement in conductivity was observed compared to TEMABF4.

Conductivities of binary mixtures of ionic liquids with polar solvents

Data for the conductivity, κ, of selected binary mixtures of the ionic liquids [emim][BF4], [bmim][BF4], [bmim][PF 6], [brmm][DCA], and [hmim][BF4] with polar solvents (water, propylene carbonate, dimethyl-sulfoxide, methanol, dichloromethane) at 25 °C are reported. Additionally, mixture densities, p, were determined to convert κ into molar conductivity, A. The obtained results were fitted by appropriate interpolation formulas. Where possible, data were compared with information from the literature. Electrode polarization and sample purity, including [BF4-] hydrolysis, were considered as possible sources of errors in κ. The effect of viscosity on the accuracy of p and thus A was checked.

Water-assisted stability of carbene: cyclic voltammetric investigation of 1-ethyl-3-methylimidazolium ethylsulfate ionic liquid

In this work, we report electrochemical studies on imidazolium-based ionic liquids with an objective to explore the possibility of carbene formation in their dilute aqueous solutions. Conventionally, water plays a detrimental role during investigations involving ionic liquids, and this role has been investigated via electrochemical studies in aqueous ionic liquid solutions. There are varying opinions regarding the influence of water on the physicochemical behaviour of ionic liquids that require an in-depth understanding. To eludicate the role of water, we attempted to evaluate the electrochemical performance of ionic liquids in water as a solvent, and the influence of water on ionic liquids was explored through feasibility and stability studies on carbene formed in an aqueous imidazolium-based ionic liquid solution. The electrochemical investigation of an aqueous solution of 1-ethyl-3-methylimidazolium ethylsulfate ([EMIM][EtSO4]) revealed a redox couple. Detailed investigations suggest that reduction of the imidazolium cation occurs at the C2 position, with subsequent formation of carbene. Furthermore, an anodic peak was found to be associated with the oxidation of carbene. The coulometric process associated with the anodic peaks indicated that the two-electron oxidation of carbene occurred. The stability of carbene in water was evaluated through the use of different protic and aprotic solvents. The hydrogen bond-forming ability of carbene with water seems to be responsible for its improved stability in water.

Deciphering the anthelmintic activity of benzimidazolium salts by experimental and in-silico studies

Inspired from the facts that majority of the drug administrated in the form of salts and “poison is in the dose”; herein, we have synthesized and characterized 1-methyl-3-alkylbenzimidazolium and 1-methyl-3-alkylimidazolium derived ionic salts with varying N-alkyl chains and different anions. These ionic salts were evaluated for their vermicidal activity (VA) and cell viability test against the Pheretima posthuma and A549 cell lines (human alveolar basal epithelial cells), respectively. The morphological changes in the test organism were visualized by the Scanning Electron Spectroscopy (SEM) to get the mechanistic insight. Furthermore, results were compared with VA of 1-methyl-3-alkylimidazolium derivatives to establish their structure-activity-relationship (SAR) of the fused benzene ring in 1-methyl-3-alkylimidazolium. The current findings suggested that the activity of these salts depends on the nature of N-alkyl side-chain, anionic moieties, varying partial charge on quaternary nitrogen (due to different anions) lipophilicity and types of cationic core fused with imidazolium ring. These findings were complemented by the quantitative-structure-activity-relationship (QSAR), molecular docking approaches to unfold the features accountable for their activities and binding patterns of the ligand-receptor complex respectively. ADME/T assessment of the ionic salts shows that twelve compounds qualified the ADMET profiling test & encompasses the drug-likeness features.

Lewis Acid Catalyzed Synthesis of Cyanidoborates

The reactions of [BF4]- salts with Me3SiCN were studied at different temperatures and in the presence of several different Lewis acids, which led to the generation of the well-known [BF4-n(CN)n]- (n = 1-4) salts. Depending on the catalyst and the reaction conditions, the whole series of [BF4-n(CN)n]- salts is now accessible under ambient conditions, and long preparation times and the excessive production of waste materials can be avoided. The best results were obtained when the F-/CN- substitution reactions were performed in ionic liquids.

Interactions of CO2 with the homologous series of СnMIMBF4 ionic liquids studied in situ ATR-FTIR spectroscopy: spectral characteristics, thermodynamic parameters and their correlation

In this work, in situ ATR-FTIR spectroscopy was used to study the interaction of CO2 and a series of 1-alkyl-3-methylimidazolium tetrafluoroborate СnMIMBF4 (n = 2, 4, 6, 8, 10) ionic liquids. A detailed analysis of the infrared spectra acquired from ionic liquids and sorbed СО2 was performed as ionic liquids with different the alkyl chain lengths were subjected to changing pressures of СО2 and temperature. With a longer alkyl chain length, an increase in the shift of the CH stretching vibrations bands of alkyl groups and BF stretching vibrations of BF4? anions is observed during CO2 sorption. This indicates the disaggregation of alkyl chains and anions. There is a correlation with the position of the wavenumber of the ν3 asymmetric stretching CO2 band and the length of the alkyl chain. It was found that some of the CO2 adsorbed by ionic liquids does not interact with the ionic liquid but is “free” in the bulk of the alkyl chains. For the first time, ATR-FTIR spectroscopy was used to determine the thermodynamic parameters of CO2 sorption in ionic liquids. It was demonstrated that the values of enthalpy and entropy obtained by analysis of the ATR-FTIR spectra are consistent the data obtained by other methods. A correlation was found between the enthalpy of sorption of CO2 and the wavenumber of the ν3 band. This opens up the possibility of using CO2 as an IR-sensitive probe molecule to characterize the acid-base properties of ionic liquids and determine the enthalpy of CO2 sorption.

Heteronuclear NOE spectroscopy of ionic liquids

19F,1H HOESY experiments with three ionic liquids ([bmim]BF4, [bmim]PF6 and [emim]BF4) were run in two different solvents and neat. The results give preferred probabilities of presence and enable us to systematically study interactions between the cations and the anions in the ionic liquid phase by NMR spectroscopy. The influence of different solvents and of the presence or absence of air (i.e. oxygen) is discussed. This enabled us to substantially speed up the NMR experiments and to develop a more precise method for the investigation of liquid-phase structures in ionic liquids. Copyright

Correlation between hydrogen bond basicity and acetylene solubility in room temperature ionic liquids

Room temperature ionic liquids (RTILs) are proposed as the alternative solvents for the acetylene separation in ethylene generated from the naphtha cracking process. The solubility behavior of acetylene in RTILs was examined using a linear solvation energy relationship based on Kamlet-Taft solvent parameters including the hydrogen-bond acidity or donor ability (α), the hydrogen-bond basicity or acceptor ability (β), and the polarity/polarizability (π*). It is found that the solubility of acetylene linearly correlates with β value and is almost independent of α or π*. The solubility of acetylene in RTILs increases with increasing hydrogen-bond acceptor (HBA) ability of the anion, but is little affected by the nature of the cation. Quantum mechanical calculations demonstrate that the acidic proton of acetylene specifically forms hydrogen bond with a basic oxygen atom on the anion of a RTIL. On the other hand, although C-H???π interaction is plausible, all optimized structures indicate that the acidic protons on the cation do not specifically associate with the π cloud of acetylene. Thermodynamic analysis agrees well with the proposed correlation: the higher the β value of a RTIL is, the more negative the enthalpy of acetylene absorption in the RTIL is.

A novel method for preparation of imidazolium tetrafluoroborate ionic liquids

A new method for the preparation of substituted imidazolium tetrafluoroborate salt, some of which are known as versatile room temperature ionic liquids, is proposed. The new method based on N-methylation of imidazole provided tetrafluoroborate derivatives containing no counterions, with shorter time and lower cost than conventional ion-exchange method.

Alternative route to metal halide free ionic liquids

An alternative synthetic route to metal halide free ionic liquids using trialkyloxonium salt is proposed. Utility of this synthetic route has been demonstrated by preparing 1-ethyl-3-methylimidazolium tetrafluoroborate ionic liquid through the reaction be

Separation of ethyl acetate and ethanol by room temperature ionic liquids with the tetrafluoroborate anion

Liquid-liquid equilibrium data are presented for mixtures of 1-ethyl-3-methylimidazolium tetrafluoroborate ([emim]BF4) or 1-(2-hydroxyethyl)-3-methylimidazolium tetrafluoroborate ([C2OHmim] BF4) or 1-ethyl-2,3-dimethylimidazolium tetrafluoroborate ([edmim]BF4) or 1-(2-hydroxyethyl)-2,3-dimethylimidazolium tetrafluoroborate ([C2OHdmim]BF4) + ethanol + ethyl acetate at 298.15 K. The distribution ratio and selectivity values, derived from the tie line data, show that [C2OHmim]BF4 has better extraction capacity than other studied ionic liquids and that a hydroxyl group on the cation and a CH3 group at the 2-position can obviously affect the interaction between the ionic liquid and ethanol. The experimental results show that [C2OHmim]BF4 is potentially a candidate to separate ethyl acetate and ethanol by liquid-liquid extraction. The experimental tie lines were correlated with the NRTL equation.

Four fluoroborates ion liquid synthetic method of the (by machine translation)

The invention discloses a four-tetrafluoroborate ionic liquid synthetic method, comprises the following steps: the molar ratio of 1:1 - 7 of the quaternized substrate with the alkyl halide dispersed in a solvent, in the 30 - 50 °C lower, by UV-irradiation, the illumination intensity for 10 - 1000 W/m2 , Irradiation time is 8 - 12 is H, to obtain the quaternary ammonium salt solution; the quaternary ammonium salt solution with four fluoroborates mix, in the 35 - 45 °C lower, by UV-irradiation, the illumination intensity for 10 - 1000 W/m2 , Irradiation time is 16 - 20 the H, get mixed solution; filtering the mixed solution, to obtain the filtrate, the filtrate is heated and concentrated, to remove the solvent, to obtain four tetrafluoroborate ionic liquid. The invention by UV-irradiation and heating way to synthesize four tetrafluoroborate ionic liquid, yield and the reaction rate is high. (by machine translation)

Quaternary ammonium salt preparation method

The invention provides a quaternary ammonium salt preparation method which comprises the preparation steps: (1) making amine and acid react to generate amine salt; (2) making the amine salt and alkylcarbonate react in an organic solvent to generate quaternary ammonium salt; (3) purifying a product in the step (2) by a crystallizing method to obtain corresponding quaternary ammonium salt. No halide takes part in a reaction process of the method, so that a content of halide ions in the quaternary ammonium salt is smaller than 5ppm; super capacitor electrolyte prepared from the quaternary ammonium salt has excellent cycling performance.