174501-65-6

Basic information

• Product Name: 1-Butyl-3-methylimidazolium tetrafluoroborate
• Synonyms: 1-N-BUTYL-3-METHYLIMIDAZOLIUM TETRAFLUOROBORATE;1-Butyl-3-methylimidazoliumtetrafluoroborate,98%[BMIM][BF4];1-n-Butyl-3-methylimidazolium tetrafluoroborate, 98+%;1-Butyl-3-methylimidazolium tetrafluoroborate ,99%;1-Butyl-3-methylimidazolium terafluoroborate;1-Butyl-3-methylimidazolium tetrafluoroborate,BMIMBF4;1-Butyl-3-methylimidazolium tetrafluoroborate,BMIMBF4, Basionics EE 04;1-Butyl-3-methylimidazolium tetrafluoroborate, 98+%
• CAS NO: 174501-65-6
• Molecular Formula: BF₄*C₈H₁₅N₂
• Molecular Weight: 226.02
• EINECS: 1308068-626-2
• Product Categories: Imidazolium Compounds;Imidazolium Salts (Ionic Liquids);Ionic Liquids;Synthetic Organic Chemistry;organic amine salt;Chemical Synthesis;Imidazolium;Specialty Synthesis
• Mol File: 174501-65-6.mol

Chemical Properties

• Melting Point: -71 °C
• Flash Point: 288 °C
• Appearance: Clear yellow-orange/Viscous Liquid
• Density: 1.21 g/mL at 20 °C(lit.)
• Refractive Index: n20/D 1.52
• Storage Temp.: Store below +30°C.
• Water Solubility: Miscible with acetone, acetonitrile, ethyl acetate, isopropyl alcohol and methylene chloride. Immiscible with hexane, toluene an
• Stability: hygroscopic
• CAS DataBase Reference: 1-Butyl-3-methylimidazolium tetrafluoroborate(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Butyl-3-methylimidazolium tetrafluoroborate(174501-65-6)
• EPA Substance Registry System: 1-Butyl-3-methylimidazolium tetrafluoroborate(174501-65-6)

Safety Data

• Hazard Codes: Xn,Xi,N,T
• Statements: 22-36/37/38-51/53-36/38-25
• Safety Statements: 37/39-26-61-45
• RIDADR: UN2810 6.1/PG 3
• WGK Germany: 3
• F: 10-21
• HazardClass: 9
• PackingGroup: Ⅲ
• Hazardous Substances Data: 174501-65-6(Hazardous Substances Data)

Usage

Uses

Used in Chemical Reactions:
1-Butyl-3-methylimidazolium tetrafluoroborate is used as a solvent for various organic reactions, including hydrogenations and asymmetric hydrogenations, which proceed with higher enantioselectivity than in homogeneous phase. It is also used in Suzuki cross-coupling reactions.
Used in Extractive Desulfurization:
1-Butyl-3-methylimidazolium tetrafluoroborate may be used as an extractant for the removal of dibenzothiophene (DBS) from liquid fuels via extractive desulfurization.
Used in the Preparation of NH4TiOF3 Mesocrystals:
1-Butyl-3-methylimidazolium tetrafluoroborate can be used as a reaction medium for the preparation of NH4TiOF3 mesocrystals, which are then converted into TiO2-based nanostructures.
Used in Absorption Heat Pumps or Chillers:
1-Butyl-3-methylimidazolium tetrafluoroborate can be used as a working fluid along with 2,2,2-trifluoroethanol in absorption heat pumps or chillers.
Used in Energy Storage Devices:
1-Butyl-3-methylimidazolium tetrafluoroborate can be used as an electrolyte in lithium-ion batteries and double-layer capacitors.
Note: 1-Butyl-3-methylimidazolium hexafluorophosphate, also known as BMIM-PF6, is a related ionic liquid that is viscous, colorless, hydrophobic, and non-water-soluble with a melting point of -8°C. It is also one of the most widely studied ionic liquids and is known to very slowly decompose in the presence of water.

solubility

Miscible with acetone, acetonitrile, ethyl acetate, isopropyl alcohol and methylene chloride. Immiscible with hexane, toluene and water.

InChI:InChI=1/C8H15N2.BF4/c1-3-4-5-10-7-6-9(2)8-10;2-1(3,4)5/h6-8H,3-5H2,1-2H3;/q+1;-1

Upstream product

• 50-00-0 formaldehyd 
• 131543-46-9 Glyoxal 
• 109-73-9 N-butylamine 
• 74-89-5 methylamine 
• 616-47-7 1-methyl-1H-imidazole 
• 109-69-3 n-Butyl chloride 
• 109-65-9 1-bromo-butane 
• 4316-42-1 1-Butylimidazole 
• 616-38-6 carbonic acid dimethyl ester 
• 13755-29-8 sodium tetrafluoroborate 
• 79917-90-1 1-butyl-3-methylimidazolium chloride 
• 14075-53-7 potassium tetrafluoroborate 
• 149-73-5 trimethyl orthoformate 
• 13826-83-0 ammonium tetrafluroborate 

Downstream Products

• 4316-42-1 1-Butylimidazole 
• 1126-80-3 (n-butylthio)benzene 
• 100-68-5 methyl-phenyl-thioether 
• 13910-18-4 (n-decylthio)benzene 
• 93-58-3 benzoic acid methyl ester 
• 136-60-7 benzoic acid, butyl ester 
• 56056-49-6 (n-dodecylthio)benzene 
• 1126-78-9 N-(n-butyl)aniline 
• 121-69-7 N,N-dimethyl-aniline 
• 100-61-8 N-methylaniline 
• 100-66-3 methoxybenzene 
• 1534-08-3 S-methyl thiolacetate 
• 928-47-2 S-butyl ethanethioate 
• 119393-94-1 1-butyl-3-methyl-1H-imidazole-2(3H)-thione 

Relevant articles and documents

Volumetric properties of 1-butyl-3-methylimidazolium tetrafluoroborate- glucose-water systems

Densities for 1-butyl-3-methylimidazolium tetrafluoroborate ([Bmim]BF 4)-glucose-water solutions were determined at 298.15 K. The measured densities were used to calculate the apparent molar volumes of glucose (V Φ,S) and [Bmim]BFsu

Electrochemistry of 1-butyl-3-methyl-1H-imidazolium tetrafluoroborate ionic liquid

The electrochemistry of 1-butyl-3-methyl-1H-imidazolium tetrafluoroborate (BmimBF4) ionic liquid was investigated by cyclic voltammetry and Osteryoung square wave voltammetry. Impurity chloride was identified, its concentration was determined and a way to eliminate it was demonstrated. Constant current electrolysis of BmimBF4 was performed and products were analyzed by 1H, 13C, and 19F-NMR and gas chromatography-mass spectrometry. BF3 and fluorocarbons are produced at the anode while Bmim+ undergoes dimerization and dealkylation reactions at the cathode after reduction to a carbene.

Crystallographic Insights into the Behavior of Highly Acidic Metal Cations in Ionic Liquids from Reactions of Titanium Tetrachloride with [1-Butyl-3-Methylimidazolium][X] Ionic Liquids (X = Chloride, Bromide, Tetrafluoroborate)

Highly charged metal ions are difficult to investigate in weakly coordinating ionic liquids (ILs) because of the insolubility of their solid forms, but the molecular liquid TiCl4 offers a way to react tetravalent metal ions in an IL. Reactions of TiCl4 with 1-butyl-3-methylimidazolium ([C4mim]+)-based ILs containing chloride or bromide lead to mixtures of highly metastable amorphous solids and small amounts of crystalline chlorotitanate salts including [C4mim]2[TiCl6] and two polymorphs of [C4mim]2[Ti2Cl10] in a manner not well correlated with stoichiometry or anion identity. The reaction of TiCl4 with [C4mim][BF4] yields crystals of the mixed fluoro-chloro complex [C4mim]2[Ti4F6Cl12], indicating spontaneous reaction of the IL ions to generate HF in situ. These unusual behaviors are explained in terms of the exceptionally high acidity of Ti4+ and the unusual behavior of TiCl4 among metal halides as a nonpolar molecular compound.

A study of halide nucleophilicity in ionic liquids

The relative nucleophilicity of chloride, bromide and iodide anions in [bmim][BF4] ionic liquid has been measured by studying their reaction with methyl p-nitrobenzenesulfonate ([bmim] = 1-butyl-3-methylimidazolium cation). It has been found that iodide is the most nucleophilic halide, and that chloride and bromide have approximately equal nucleophilicities (Cl- is slightly more nucleophilic than Br-) in [bmim][BF4]. Activation energies for the reaction of chloride and bromide with methyl p-nitrobenzenesulfonate have been calculated. The relative nucleophilicity of the halides has been compared with that observed in molecular solvents and in a tetraalkylammonium tetraalkylboride ionic liquid.

Interaction between the ionic liquids 1-alkyl-3-methylimidazolium tetrafluoroborate and Pluronic P103 in aqueous solution: A DLS, SANS and NMR study

The effect of three ionic liquids (ILs) 1-alkyl 3-methyl imidazlolium tetraflouroborates (Cnmim BF4 n = 4, 6, 8) on micellar solutions of an ethylene oxide-propylene oxide block copolymer (PEO-PPO-PEO), Pluronic P103 was examined from scattering and NMR techniques. The ILs alter the cloud point and micelle size dependant on their alkyl chain length and the results are discussed in terms of their behavior as cosolvent/cosurfactant. Cloud point data support the hydrogen bonding between the imidazolium cation and P103 while dynamic light scattering (DLS) and small angle neutron scattering (SANS) reveal that presence of ionic liquid is not conducive to the micelle formation of P103. The selective nuclear Overhauser effect (NOESY) indicates that the PPO block of the P103 interacts with the alkyl group of the C nmim+ cation by hydrophobic interaction. Through this kind of interactions, Cnmim BF4 and P103 can form mixed micelles. This result indicates that the presence of ILs hinders the micelle formation of P103 in solution and promotes P103 to orient at air/water interface.

Determination of residual chloride content in ionic liquids using LA-ICP-MS

Nowadays, ionic liquids (ILs) are used in a wide range of applications. Their exceptional chemical and physical properties, sustainability of use and the possibility of easy recycling are attractive aspects promoting the acceptance of ILs also for commercial applications. While synthesis is in most cases simple and straightforward, purification of the reaction products might pose a number of problems. Due to the major influence of inorganic contaminations from the synthesis process, thorough monitoring of impurities is required. However, the unusual properties of ILs create some problems for conventional chemical analysis. In this work, a dried droplet approach with subsequent LA-ICP-MS sampling will be used for the analysis of chloride in ILs-a by-product from the synthesis procedure. Dried droplet application onto pre-cut filter paper disks allows the analysis of hydrophilic as well as hydrophobic ILs with calibration from dried aqueous standards for signal quantification. The approach is applied on two types of alkylimidazolium ILs, underlining the versatility of the sample preparation and measurement approach. Compared to commonly used analysis techniques for chloride in ILs, the presented approach is simple, fast, and does not require harmful reagents. Different internal standardization strategies were investigated during this study. With a reproducibility of below 2% relative standard deviation and limits of detection of 0.09 mg g-1 for chloride in ILs, the presented approach was showed to be fit for the purpose of routine analyses and reaction monitoring. If necessary, the approach can be extended to other analytes of interest in the field of the synthetic chemistry of ILs.

Thermodynamics of cesium complexes formation with 18-crown-6 in ionic liquids

Thermodynamic data for cesium complexes formation with 18-crown-6 (18C6, L) [Cs(18C6)]+ in N-butyl-4-methyl-pyridinium tetrafluoroborate ([BMPy][BF4], I), in 1-butyl-3-methylimidazolium tetrafluoroborate ([BMIM][BF4], II) and in 1-butyl-3-methylimidazolium dicyanamide ([BMIM][N(CN)2], III) were measured with NMR 133Cs technique at 23-50 °C. The stability of cesium complex in RTILs is estimated to be in the range between water and DMFA. Stability constants for [Cs(18C6)]+ are found to decrease as temperature is increasing. The following values for lgK(Cs+L) and ΔH(Cs+L) at 23 °C are determined: 2.6 (0.3), -47(1) kJ/mol (RTIL I); 2.8(0.3), -80(3) kJ/mol (RTIL II) and 3.03 (0.08), -47(2) kJ/mol (RTIL III). It is demonstrated that enthalpy change promotes complex formation while the corresponding change of entropy is negative and provides decomposition of [Cs(18C6)]+.

A silver and water free metathesis reaction: A route to ionic liquids

A versatile, cheaper, silver and water-free metathesis reaction was developed for imidazolium, phosphonium and pyrrolidinium based ionic liquids (ILs) associated with different anions such as dicyanamide, thiocyanate, tetrafluoroborate and bis(trifluoromethylsulfonyl)imide. This route, using the melt of amine chloride as a solvent and reagent, favours the ion exchange reaction using anion salts of Na or Li, yielding ionic liquids in high purity (≥99.5%) and high yields (≥90%). This route is particularly well adapted for water miscible ILs preparation.

A facile and efficient route to hydrophilic ionic liquids through metathesis reaction performed in saturated aqueous solution

The preparation of ionic liquids most often involves the use of organic solvents or hazardous chemicals, especially for hydrophilic ionic liquids prepared from metathesis reaction. In this study, the salting-out effect was proposed to promote the metathesis reaction to afford water-miscible ionic liquids. The reaction proceeds in aqueous solution saturated with an inorganic precursor salt. After reaction for only 10 min, the hydrophilic product can be easily obtained by spontaneous liquid-liquid phase-separation caused by the salting-out effect, followed by concentration and filtration. In this process, no organic solvents or hazardous chemicals are required, and the saturated solution and inorganic by-product can be easily reused and recycled respectively.

Comparative Investigation of the Ionicity of Aprotic and Protic Ionic Liquids in Molecular Solvents by using Conductometry and NMR Spectroscopy

Electrical conductivity (σ), viscosity (η), and self-diffusion coefficient (D) measurements of binary mixtures of aprotic and protic imidazolium-based ionic liquids with water, dimethyl sulfoxide, and ethylene glycol were measured from 293.15 to 323.15 K. The temperature dependence study reveals typical Arrhenius behavior. The ionicities of aprotic ionic liquids were observed to be higher than those of protic ionic liquids in these solvents. The aprotic ionic liquid, 1-butyl-3-methylimidazolium tetrafluoroborate, [bmIm][BF4], displays 100 % ionicity in both water and ethylene glycol. The protic ionic liquids in both water and ethylene glycol are classed as good ionic candidates, whereas in DMSO they are classed as having a poor ionic nature. The solvation dynamics of the ionic species of the ionic liquids are illustrated on the basis of the 1H NMR chemical shifts of the ionic liquids. The self-diffusion coefficients D of the cation and anion of [HmIm][CH3COO] in D2O and in [D6]DMSO are determined by using 1H nuclei with pulsed field gradient spin-echo NMR spectroscopy.