85100-78-3

Basic information

• Product Name: 1-HEXYL-3-METHYLIMIDAZOLIUM BROMIDE
• Synonyms: 1-HEXYL-3-METHYLIMIDAZOLIUM BROMIDE;1-Hexyl-3-methylimidazolium bromide,99%;1-hexyl-3-Methyl-1H-iMidazol-3-iuM broMide;1-hexyl-3-MethyliMidazoliuM briMide;1-Hexyl-3-methyimidazolium Bromide;[HMIM]Br;1-Hexyl-3-methylimidazoliumBromide,98%
• CAS NO: 85100-78-3
• Molecular Formula: Br*C₁₀H₁₉N₂
• Molecular Weight: 247.18
• Product Categories: Imidazolium Compounds;Imidazolium Salts (Ionic Liquids);Ionic Liquids;Synthetic Organic Chemistry
• Mol File: 85100-78-3.mol
• Article Data: 95

Chemical Properties

• Melting Point: -54.9 °C
• Boiling Point: 395 °C (6 mmHg)
• Appearance: clear yellow to yellow-brown viscous liquid
• Density: 1.23
• Refractive Index: 1.532-1.534
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: 1-HEXYL-3-METHYLIMIDAZOLIUM BROMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-HEXYL-3-METHYLIMIDAZOLIUM BROMIDE(85100-78-3)
• EPA Substance Registry System: 1-HEXYL-3-METHYLIMIDAZOLIUM BROMIDE(85100-78-3)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-22
• Safety Statements: 37/39-26-24/25
• Hazardous Substances Data: 85100-78-3(Hazardous Substances Data)

Usage

Chemical Properties

clear yellow to yellow-brown viscous liquid

Uses

1-Hexyl-3-methylimidazolium bromide is a compound that is produced as part of industrial processes, then released into the environment. 1-Hexyl-3-methylimidazolium bromide is toxic to freshwater algae, plankton and other aquatic organisms. 1-Hexyl-3-methylimidazolium bromide also possesses some antimicrobial activity.

InChI:InChI=1/C10H19N2.BrH/c1-3-4-5-6-7-12-9-8-11(2)10-12;/h8-10H,3-7H2,1-2H3;1H/q+1;/p-1

Upstream product

• 616-47-7 1-methyl-1H-imidazole 
• 111-25-1 1-bromo-hexane 
• 74-83-9 methyl bromide 
• 33529-01-0 1-hexylimidazole 
• 5587-42-8 imidazolyl sodium 

Downstream Products

• 244193-50-8 1-hexyl-3-methylimidazolium tetrafluoroborate 
• 111-25-1 1-bromo-hexane 
• 382150-50-7 1-hexyl-3-methylimidazolium bis-(trifluoromethanesulfonyl)amide 
• 304680-35-1 1-hexyl-3-methylimidazolium hexafluorophosphate 
• 847499-74-5 1-hexyl-3-methylimidazolium thiocyanate 
• 478935-29-4 1-hexyl-3-methylimidazolium hydrogen sulphate 
• 171058-17-6 1-hexyl-3-methylimidazol-1-ium chloride 

Relevant articles and documents

Fluid-phase behavior of {1-hexyl-3-methylimidazolium bis(trifluoromethylsulfonyl) imide, [C6mim][NTf2], + C2-C8 n-alcohol} mixtures: Liquid-liquid equilibrium and excess volumes

In the frame of the IUPAC Project entitled Thermodynamics of ionic liquids, ionic liquid mixtures, and the development of standarized systems, 1-hexyl-3-methylimidazolium bis(trifluoromethylsulfonyl) imide, [C 6mim][NTf2], was selected as the model ionic liquid to perform round-robin measurements on a series of ionic liquid properties. In this work, the temperature-composition liquid-liquid equilibria of this ionic liquid with linear alkan-1-ols, CnH(2n+1)OH, with n = 4, 5, 6, and 8, were determined at a nominal pressure of 0.1 MPa and up to 50 MPa for n = 4, 5, and 6. Excess molar volumes, VE, of mixtures of this same ionic liquid with linear alkan-1-ols, CnH 2n+1OH, with n ranging from 2 to 5, were measured at a nominal pressure of 0.1 MPa. The consistency between the two sets of experimental data (phase diagrams and VE) was analyzed from a theoretical perspective; we noticed that as the alkyl chain length, n, of the linear alcohol varies both the pressure dependence of the phase diagrams and the critical excess molar volume change sign.

A rapid dispersive liquid-liquid microextraction based on hydrophobic deep eutectic solvent for selective and sensitive preconcentration of thorium in water and rock samples: A multivariate study

Thorium [Th(IV)] and its compounds are highly toxic and cause severe damage to bone and kidney through long term exposures. Conventional methods of Th(IV) detection are complicated and costly. In this study, we developed a new dispersive liquid-liquid microextraction (DLLME) based on hydrophobic deep eutectic solvent (HDES) for preconcentration of Th(IV) in water and rock samples prior to UV–Vis. spectrophotometric detection. The microextraction procedure was carried out by applying thorin as a chelating agent, cethyltrimethyl ammonium bromide (CTAB) as an ion pairing agent and a DES consisted of 1-hexyl-3-methylimidazolium and salicylic acid components as an extraction solvent. Central composite design (CCD) was applied to obtain the best condition of the microextraction procedure. The developed method is a green, facile, fast, selective and sensitive that could detect Th(IV) in the concentration range of 10–600 ng mL?1 with a limit of detection (LOD) and preconcentration factor of 2.1 ng mL?1 and 59, respectively. The relative standard deviation of five replicate measurements of Th(IV) at 100 ng mL?1 was 1.7%. Finally, the proposed method was successfully applied to the analysis of Th(IV) in water and rock samples, and desirable results were obtained.

Exploration of the solvation behavior of the synthesized 1-hexyl-3-methylimidazolium bromide [C6mim][Br] ionic liquid with L-cysteine and N-acetyl L-cysteine) in aqueous medium at different temperatures

The interactions of L-cysteine and N-acetyl L-cysteine with imidazolium-based ionic liquid 1-hexyl-3-methylimidazolium bromide [C6mim] [Br] as a function of temperature have been studied by a combination of volumetric and acoustic properties. Densities and speeds of the sound of L-cysteine and N-acetyl L-cysteine in (0.00, 0.005, 0.01, 0.03 and 0.05) mol.kg?1 aqueous solutions of 1-hexyl-3-methylimidazolium bromide have been measured at T = (288.15, 298.15, 308.15 and 318.15) K. From density data, the apparent molar volume (V?) the partial molar volume (V?0) and standard partial molar volumes of transfer (ΔV?0) for L-cysteine and N-acetyl L-cysteine from water to aqueous 1-hexyl-3-methylimidazolium bromide solutions have been calculated. Partial molar isentropic compression (K?,s) and partial molar isentropic compression of transfer (ΔK?, S0) have been calculated from the speed of sound data. The pair and triplet interaction coefficient have been calculated from both these properties. The parameters obtained have been used to describe the results in terms of (solute-solute), (solute-solvent) interactions, structure building and structure floating behavior of amino acids in aqueous 1-hexyl-3-methylimidazolium bromide solutions.

Deciphering aggregation behavior and thermodynamic properties of anionic surfactant sodium hexadecyl sulfate in aqueous solutions of ionic liquids [C5mim][Br] and [C6mim][Br]

The present work aims to study the interactions of cationic imidazolium based ionic liquids i.e. 1-alkyl-3-methylimidazolium bromide ([Cnmim][Br], where n = 5 &6) with anionic surfactant sodium hexadecyl sulfate (SHS) in aqueous media employing the various techniques such as conductivity measurement, fluorescence spectroscopy, UV–visible spectroscopy and FT-IR spectroscopy. The temperature dependence of critical micelle concentration (CMC) determined using conductivity measurements at temperatures (298.15, 303.15 and 308.15) K at different concentrations (0.02, 0.05 and 0.1) wt. %, of ionic liquids (ILs) in aqueous medium was used to calculate the various thermodynamic parameters of micellization such as, standard free energy of micellization (ΔGm 0), standard enthalpy of micellization (ΔHm 0), and standard entropy of micellization (ΔSm 0). Further, fluorescence and UV–Visible spectroscopy have been utilized to confirm the CMC values obtained from conductivity measurements, which were found to be in good agreement. A continuous increment in CMC value was observed with the increase in concentration of ILs as well as in temperature. Further FT-IR Spectroscopic studies have been done to demonstrate the structural alterations occurring in the respective mixtures.

Light-modulated aggregation behavior of some unsubstituted cinnamate-based ionic liquids in aqueous solutions

Light modulation of the self-assembly behavior of ionic liquids in aqueous solution is of great importance from the viewpoint of fundamentals and technology. In this work, a new class of light-responsive ionic liquids composed of 1-alkyl-3-methylimidazolium cations, [Cnmim]+ (n = 4, 6, 8, 10, 12), and the trans-cinnamic acid ([CA]) anion was synthesized and characterized. These compounds were used to study the modulation action of UV light on the aggregation behavior of ionic liquids in aqueous solution. For this purpose, the critical aggregation concentration (CAC), ionization degree of the aggregates (α), standard Gibbs energy of aggregation (ΔG°m) and aggregate size of the ionic liquids were determined before and after UV light irradiation by conductivity and dynamic light scattering techniques. The percentage of cis-isomer of these ionic liquids was also reported at the photoisomerism equilibrium from HPLC measurements. It was found that the aggregation behavior of [Cnmim][CA] (n = 8, 10, 12) could be efficiently modulated by UV light in aqueous solution. After UV light irradiation, the values of CAC, α and ΔG°m increased, while the size of the aggregates decreased. These results have been rationalized from the photo-isomerization of the [CA] anion, hydrophilicity and structural features of the cis-isomer of the [CA] anion.

Interaction between Ionic Liquids and Gemini Surfactant: A Detailed Investigation into the Role of Ionic Liquids in Modifying Properties of Aqueous Gemini Surfactant

Tuning physicochemical properties of aqueous surfactant solutions comprised of normal or reverse micelles by external additives is of utmost importance due to the enormous application potential of surfactant-based systems. Unusual and interesting properties of environmentally benign ionic liquids (IL) make them suitable candidates for this purpose. To understand and establish the role of IL in modifying properties of aqueous gemini surfactants, we studied the effect of the IL, 1-hexyl-3-methylimidazolium bromide ([Hmim][Br]) and 1-octyl-3-methylimidazolium bromide ([Omim][Br]) on the properties of the aqueous cationic gemini surfactant 1,6-hexanediyl-α,ω-bis(dimethyltetradecyl)ammonium bromide (14-6-14,2Br-). The behavioral changes were investigated by measuring the critical micelle concentration (CMC) using electrical conductance, surface tension, dye solubilization and fluorescence probe measurements at 298.15 K. It was observed that the CMC of 14-6-14,2Br- gemini surfactant decreases with addition of IL, thus favoring the micellization process. An increase in micellar size was observed at lower IL concentration using dynamic light scattering, with a decrease in aggregation number (N agg) determined from fluorescence probe quenching measurements. It is noteworthy that the extent of modulation of the micellar properties is different for both the IL due to their structural differences. IL behave like electrolytes at lower concentrations and cosurfactants at higher concentrations and form mixed micelles with the cationic gemini surfactant showing an increase in N agg.

New ionic liquids with fluorous anions for supported liquid membranes and characterization

This article reports the synthesis and the characterization of novel fluorous ionic liquids with fluorous anions to be used as carrier for fluorous supported liquid membrane in view of future applications to the extraction of metal ions. Dialkylimidazoliu

The effect of 1-N-alkyl chain of ionic liquids [Cnmim] +Br- (n = 2, 4, 6, 8) on the aspect ratio of ZnO nanorods: Syntheses, morphology, forming mechanism, photoluminescence and recyclable photocatalytic activity

Using a pure ionic liquid-assisted solid-state-like synthesis method under 80 °C, high quality zinc oxide (ZnO) nanorods in 1-alkyl-3-methylimidazolium and bromide anions ionic liquids [Cnmim]+Br- (n = 2, 4, 6, 8) were rea

Low-temperature heat capacity and standard thermodynamic functions of 1-hexyl-3-methyl imidazolium perrhenate ionic liquid

Heat capacity for 1-hexyl-3-methyl imidazolium perrhenate ionic liquid [C6MIM][ReO4] in the temperature range from 79 to 396?K has been measured by a fully automated adiabatic calorimeter. For [C6MIM][ReO4], glass transition temperature, the melting temperature, standard molar heat capacity, enthalpy and entropy of solid–liquid phase transition were determined to be (202.164 ± 0.405) K, (226.198 ± 0.265) K, (480.702 ± 0.013) J?K?1?mol?1, (15.665 ± 0.195) kJ?mol?1 and (69.250 ± 0.780) J?K?1?mol?1, respectively. In addition, the thermodynamic characteristics and solid–liquid phase change behavior of [C6MIM][ReO4] were compared with the ones of [C7MIM][ReO4] reported in the literature. The thermodynamic functions (HT? H298.15), (ST? S298.15) and (GT? G298.15), for the compound in the experimental temperature range were calculated.

Electrolytic conductivity of four imidazolium-based room-temperature ionic liquids and the effect of a water impurity

The electrolytic conductivities (κ) of four hydrophobic room-temperature ionic liquids (RTILs) were measured at temperatures from (288.15 to 323.15) K. The measurements were made with a commercial conductivity cell with platinum black electrodes. In order to exclude atmospheric moisture, the conductivity cell was modified so that it could be sealed during measurements. The RTILs studied were 1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide, 1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide, 1-hexyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide, and 1-butyl-3-methylimidazolium hexafluorophosphate. The RTILs were dried under vacuum until the mass fraction of water (wH2O) was ≤10-5. Coulometric Karl Fischer titration was used to determine wH2O in each RTIL before and after measurements of κ. Most measurements were made on dried RTILs, but some measurements were performed intentionally at higher wH2O in order to study the effect of a water impurity on κ. For {water + 1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide}, κ was found to increase dramatically with increasing wH2O; for example, in going from wH2O=10-5to10-2, the fractional increase in κ was 0.36 {=(κwet - κ dried)/κdried}. This work illustrates the importance of measuring the water content in RTILs both before and after measurements of κ. Published by Elsevier Ltd.

Ionic liquids: Differential scanning calorimetry as a new indirect method for determination of vaporization enthalpies

Differential scanning calorimetry (DSC) has been used to measure enthalpies of synthesis reactions of the 1-alkyl-3-methylimidazolium bromide [C nmim][Br] ionic liquids from 1-methylimidazole and n-alkyl bromides (with n = 4, 5, 6, 7, and 8). The optimal experimental conditions have been elaborated. Enthalpies of formation of these ionic liquids in the liquid state have been determined using the DSC results according to the Hess Law. The ideal-gas enthalpies of formation of [Cnmim][Br] were calculated using the methods of quantum chemistry. They were used together with the DSC results to derive indirectly the enthalpies of vaporization of the ionic liquids under study. In order to validate the indirect determination, the experimental vaporization enthalpy of [C4mim][Br] was measured by using a quartz crystal microbalance (QCM). The combination of reaction enthalpy measurements by DSC with modern high-level first-principles calculations opens valuable indirect thermochemical options to obtain values of vaporization enthalpies of ionic liquids. ? 2012 American Chemical Society.

Quantum dots in which ionic liquids are ion-bonded and their preparation method

A quantum dot particle in which an ionic liquid is ion-bonded is disclosed. The quantum dot particle includes a quantum dot having a core/shell nanostructure; and an ionic liquid compound represented by following Chemical Formula 1, bonded to the surface of the quantum dot, wherein the quantum dot and the ionic liquid compound form an ionic bond: wherein, R1 and R2 are each independently a branched or unbranched hydrocarbon group having 1 to 22 carbon atoms, and X? is a monovalent anion, wherein the hydrocarbon group includes a saturated or unsaturated group and may include one or more hetero atoms.

ZIF-8-porous ionic liquids for the extraction of 2,2,3,3-tetrafluoro-1-propanol and water mixture

The design of stable ionic liquids (ILs) has become crucial for efficient liquid-liquid extraction (LLE) of alcohol and water. Porous ionic liquids (PILs), as a special class of ILs, have attracted attention by virtue of their unique porous structure and IL characteristics. In this research, a series of zeolitic imidazolate framework-8 based porous ionic liquids (ZIF-8-PILs) were synthesized by simply mixing a solution of zeolitic imidazolate framework-8 (ZIF-8) and rationally designed ILs. The introduction of ZIF-8 resulted in a unique liquid porous structure and molecular sieve for ZIF-8-PILs. The improved extraction properties endowed ZIF-8/[Bpy][NTf2] with more efficiency for the separation of 2,2,3,3-tetrafluoro-1-propanol (TFP) and water with 88.1% TFP extraction rate and steady reuse. The excellent extraction performance of ZIF-8-PILs is discussed in relation to their textural property and unique intermolecular interaction.