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Usage

Uses

Used in Chemical Synthesis Industry:
1-Octylimidazole is used as a catalyst for facilitating various chemical reactions, enhancing the efficiency and speed of synthesis processes.
Used in Pharmaceutical Industry:
1-Octylimidazole is used as an intermediate in the production of pharmaceuticals, contributing to the development of new drugs and medications.
Used in Plastics Industry:
1-Octylimidazole is used as a component in the manufacturing process of plastics, improving the properties and performance of the final plastic products.

InChI:InChI=1/C11H20N2/c1-2-3-4-5-6-7-9-13-10-8-12-11-13/h8,10-11H,2-7,9H2,1H3

Upstream product

• 111-86-4 n-Octylamine 
• 288-32-4 1H-imidazole 
• 629-04-9 1-Bromoheptane 
• 111-83-1 1-bromo-octane 
• 5587-42-8 imidazolyl sodium 
• 927690-63-9 1-(2-cyanoethyl)-3-octyl-1H-imidazol-3-ium bromide 
• 629-27-6 1-Iodooctane 
• 111-85-3 n-chlorooctane 
• 64777-25-9 1-octyl-1,3-dihydro-imidazole-2-thione 

Relevant academic research and scientific papers

Anticancer Activity of Polyoxometalate-Bisphosphonate Complexes: Synthesis, Characterization, in Vitro and in Vivo Results

We synthesized a series of polyoxometalate-bisphosphonate complexes containing MoVIO6 octahedra, zoledronate, or an N-alkyl (n-C6 or n-C8) zoledronate analogue, and in two cases, Mn as a heterometal. Mo6L2 (L = Zol, ZolC6, ZolC8) and Mo4L2Mn (L = Zol, ZolC8) were characterized by using single-crystal X-ray crystallography and/or IR spectroscopy, elemental and energy dispersive X-ray analysis and 31P NMR. We found promising activity against human nonsmall cell lung cancer (NCI-H460) cells with IC50 values for growth inhibition of ～5 μM per bisphosphonate ligand. The effects of bisphosphonate complexation on IC50 decreased with increasing bisphosphonate chain length: C0 ≈ 6.1×, C6 ≈ 3.4×, and C8 ≈ 1.1×. We then determined the activity of one of the most potent compounds in the series, Mo4Zol2Mn(III), against SK-ES-1 sarcoma cells in a mouse xenograft system finding a ～5× decrease in tumor volume than found with the parent compound zoledronate at the same compound dosing (5 μg/mouse). Overall, the results are of interest since we show for the first time that heteropolyoxomolybdate-bisphosphonate hybrids kill tumor cells in vitro and significantly decrease tumor growth, in vivo, opening up new possibilities for targeting both Ras as well as epidermal growth factor receptor driven cancers.

Novel alkylimidazolium ionic liquids as an antibacterial alternative to pathogens of the skin and soft tissue infections

Keeping in mind the concept of green chemistry, this research aims to synthesize and characterize new ionic liquids (ILs) derived from N-cinnamyl imidazole with different sizes of alkyl chains (1, 6, 8, and 10 carbon atoms), and evaluate their antibacterial activity against Skin and soft tissue infections (SSTIs) causative bacteria. The antibacterial screening was carried out by agar well diffusion and the Minimum Inhibitory Concentration (MIC) and Half Maximum Inhibitory Concentration (IC50) of the different ILs were determined by microdilution in broth, also Molecular dynamics simulations were performed to study the interaction mechanism between ILs and membranes. The MIC value in Gram-positive bacteria showed that as the hydrocarbon chain increases, the MIC value decreases with a dose-dependent effect. Furthermore, Gram-negative bacteria showed high MIC values, which were also evidenced in the antibacterial screening. The molecular dynamics showed an incorporation of the ILs with the longer chain (10 C), corresponding to a passive diffusion towards the membrane surface, for its part, the ILs with the shorter chain due to its lack of hydrophobicity was not incorporated into the bilayer. Finally, the new ILs synthesized could be an alternative for the treatment of Gram-positive bacteria causative of SSTIs.

Alkylation of imidazole by solid-liquid phase transfer catalysis in the absence of solvent

Phase Transfer Catalysis in the absence of solvent is described as a useful and general method for the selective N-alkylation of imidazole. In all cases high yields are obtained while quaternization is avoided.

Chemical Tuning of Zwitterionic Ionic Liquids for Variable Thermophysical Behaviours, Nanostructured Aggregates and Dual-Stimuli Responsiveness

The design and synthesis of a series of zwitterionic ionic liquids (ZILs) to understand the structure–property relationship towards an increase of the thermal stability, a variation of the glass transition temperature, the shape-tuning of nanostructured aggregates and the tuning of the stimuli responsiveness are demonstrated. The substitution reaction of imidazole with various aliphatic and aromatic bromides followed by the reaction of the corresponding substituted imidazoles with bromoalkyl carboxylic acids of varying spacer length produces the ZILs. In aqueous solution, a ZIL molecule either exist in its ionic liquid (substituted imidazolium bromide) form or its zwitterionic (substituted imidazolium alkyl carboxylate) form with an isoelectric point (pI) depending on the pH value of the solution. Upon changing the pH to near or above the pI, the aqueous ZIL solution undergoes transition from a transparent to a turbid phase due to the formation of insoluble hierarchical nanostructured aggregates of various morphologies, such as spheres, tripods, tetrapods, fern-like, flower-like, dendrites etc. depending on the pH of the solution and the nature of the alkyl/vinyl/aryl substituents. Upon heating the solution a phase transition occurs from turbid to transparent, exhibiting a distinct reversible upper critical solution temperature (UCST)-type cloud point (Tcp). It is observed that the cloud point varies with the nature of the substituent, an increase of the concentration of the ZIL as well as with changes of the pH of the solution.

Inhibition of bacterial growth and galactosyltransferase activity of WbwC by α, ω-bis(3-alkyl-1H-imidazolium)alkane salts: Effect of varying carbon content

A series of compounds was designed and synthesized having two imidazolium rings separated by a polymethylene spacer and having alkyl substituents on each of the imidazolium rings. The compounds were assayed for their effects on the activity of galactosyltransferase WbwC, and also on the growth of Gram-negative and Gram-positive bacteria, as well as human cells. The inhibition observed on enzyme activities and cell growth was dependent on the total number of carbons in the spacer and the alkyl substituents on the imidazolium rings. These readily synthesized, achiral compounds have potential as antimicrobial and antiseptic agents.

Synthesis, structure and photophysical properties of complexes [1-(9-anthracylmethyl)-3-alkylimidazol-2-ylidene]2Pt(C≡CPh) 2

1-(9-Anthracenylmethyl)-3-octylimidazolium chloride (1a) or 1-(9-anthracenylmethyl)-3-ethylimidazolium iodide (1b) was treated with (cod)Pt(CCPh)2 to afford the luminescent complexes [1-(9-anthracylmethyl)-3-alkylimidazol-2-ylidene]2

Fluoroalkylated N-heterocyclic carbene complexes of palladium

Fluoroalkylated N-heterocyclic carbene complexes of palladium have been synthesized from imidazolium salts and Pd(OAc)2. The analogous carbene complexes bearing long alkyl chains have also been prepared. The formation of these carbene complexes proceeds via an intermediate binuclear species, which has been isolated. Complexes such as these may find applications in catalysis in supercritical CO2 (scCO2).

CO2/N2 triggered Switchable surfactants with imidazole group

In order to overcome the hydrolysis of 2-alkyl-1-hydroxyethyl imidazoline and its unsatisfactory emulsification-demulsification switchability to water-alkane, the long-chain N-alkylimidazole compounds were synthesized by n-octyl bromide, n-decyl bromide, n-dodecyl bromide, n-tetradecyl bromide and n-hexadecyl bromide with imidazole, respectively and characterized by MS, 1H NMR and FTIR. The long-chain N-alkylimidazole compounds can be reversibly transformed into charged surfactants by exposure to CO2. Surface tension values indicated that N-alkylimidazolium bicarbonates had excellent surface activity compared with corresponding conventional surfactants with a lower γ CMC. The surface behaviors of the five surfactants can be illustrated by A min. Five conductivity cycles by bubbling CO2 and N2 alternately indicated that these surfactants could be switched by CO2 reversibly and repeatedly. Emulsions were repeatedly stabilized for five cycles by N-alkylimidazolium bicarbonate and broken by bubbling N2 through the solutions to reverses the reaction, releasing CO2.

A Comprehensive Study on the Synthesis and Micellization of Disymmetric Gemini Imidazolium Surfactants

Two groups of disymmetric Gemini imidazolium surfactants, [C14C4Cmim]Br2 (m?=?10, 12, 14) and [CmC4Cnim]Br2 (m?+?n?=?24, m?=?12, 14, 16, 18) surfactants, were synthesized and their structures were confirmed by 1H NMR and ESI–MS spectroscopy. Their adsorption at the air/water interface, thermodynamic parameters and aggregation behavior were explored by means of surface tension, electrical conductivity and steady-state fluorescence. A series of surface activity parameters, including cmc, γcmc, πcmc, pC20, cmc/C20, Γmax and Amin, were obtained from surface tension measurements. The results revealed that the overall hydrophobic chain length (Nc) for [C14C4Cmim]Br2 and the disymmetry (m/n) for [CmC4Cnim]Br2 had a significant effect on the surface activity. The cmc values decreased with an increase of Nc or m/n. The thermodynamic parameters of micellization (ΔGm θ, ΔHm θ, ΔSm θ) derived from the electrical conductivity indicated that the micellization process of [C14C4Cmim]Br2 and [CmC4Cnim]Br2 was entropy-driven at different temperatures, but the contribution of ΔHm θ to ΔGm θ was enhanced by increasing Nc or m/n. The micropolarity and micellar aggregation number (Nagg) were estimated by steady-state fluorescence measurements. The results showed that the surfactant with higher Nc or m/n can form larger micelles, due to a tighter micellar structure.

Aggregation of double-tailed ionic liquid 1,3-dioctylimidazolium bromide and the interaction with triblock copolymer F127

The aggregation of ionic liquid-based double-tailed surfactant, 1,3-dioctylimidazolium bromide ([Doim]Br) and its interaction with pluronic copolymer F127 were systematically investigated by nuclear magnetic resonance (NMR), surface tension, dynamic light scattering (DLS), and isothermal titration calorimetry (ITC). It was found that the [Doim]Br aggregates are composed with the alkyl chains embedded in the micellar core and with the imidazolium rings parallel and staggered on the hydrophilic layer of micelles, which was generally different from the single-tailed IL [omim]Br. The hydrogen bonding between protons attached to the imidazolium rings and anion Br- was enhanced upon the aggregation of [Doim]Br. The aggregation of F127 was promoted by addition of [Doim]Br, which was more efficient than the single-tailed surfactant. At lower [Doim]Br content, [Doim]Br monomers embedded deeply into F127 micelle core. At higher [Doim]Br concentrations, the F127 micelles were disassociated, and then F127 chains penetrated into [Doim]Br micelle. In addition, the microstructure of F127/[Doim]Br complex can also be tuned by temperature. ? 2013 American Chemical Society.