33529-01-0

Usage

Uses

Used in Corrosion Inhibition:
1-Hexylimidazole is used as a corrosion inhibitor to protect metals from degradation in various industrial settings. Its ability to form a protective film on metal surfaces helps in reducing corrosion rates and extending the service life of metal components.
Used as a Solvent:
In the chemical industry, 1-hexylimidazole serves as a solvent for various organic compounds. Its unique properties allow it to dissolve a wide range of substances, making it a versatile solvent for different applications.
Used in Pharmaceutical Synthesis:
1-Hexylimidazole is used as a building block in the synthesis of pharmaceuticals and other organic compounds. Its chemical structure provides a foundation for the development of new drugs and therapeutic agents.
Used in Coatings and Adhesives Manufacturing:
1-Hexylimidazole is employed in the production of coatings and adhesives, contributing to their performance characteristics such as adhesion, durability, and resistance to environmental factors. Its presence in these formulations enhances the overall quality and effectiveness of the final products.

Upstream product

• 288-32-4 1H-imidazole 
• 544-10-5 1-Chlorohexane 
• 111-25-1 1-bromo-hexane 
• 110-53-2 1-Bromopentane 
• 2232-08-8 N-tosylimidazole 
• 111-27-3 hexan-1-ol 
• 16156-50-6 n-hexyl methanesulfonate 
• 5587-42-8 imidazolyl sodium 
• 638-45-9 1-Iodohexane 

Downstream Products

• 1431720-85-2 N-hexyl-N-((Z)-2-{[(Z)-3-oxo-1,3-diphenyl-1-propenyl]amino}ethenyl)formamide 
• 439937-61-8 1-(1-butyl-3-imidazolio)butane-4-sulfonate 
• 1361182-31-1 1-hexylimidazolium picrate 

Relevant academic research and scientific papers

N-Functionalised Imidazoles as Stabilisers for Metal Nanoparticles in Catalysis and Anion Binding

Metal nanoparticles (NPs) have physicochemical properties which are distinct from both the bulk and molecular metal species, and provide opportunities in fields such as catalysis and sensing. NPs typically require protection of their surface to impede aggregation, but these coatings can also block access to the surface which would be required to take advantage of their unusual properties. Here, we show that alkyl imidazoles can stabilise Pd, Pt, Au, and Ag NPs, and delineate the limits of their synthesis. These ligands provide an intermediate level of surface protection, for which we demonstrate proof-of-principle in catalysis and anion binding.

Structure and properties of N, N-alkylene bis(Na?2-alkylimidazolium) salts

A series of N,N-alkylene bis(Na?2-alkylimidazolium) salts with various anions was prepared and characterized. The hydrogen-bonding abilities and ion-pairing strengths of the salts in solution were varied by changing the solvent and anion. Qualitatively, the extent of ion pairing of the 1,2-bis[N-(Na?2-butylimidazolium)]ethane salts with different anions was determined in acetone-d6 by 1H NMR spectroscopy. Thermal properties of the imidazolium salts were related not only to the nature of anions but also to the spacer length between imidazolium cations. Exceptionally high melting points of 1,2-bis[N-(Na?2-alkylimidazolium)]ethane bis(hexafluorophosphate)s can be explained by multiple hydrogen bonds observed in the X-ray crystal structures. Moreover, a trans conformation of the ethylene spacer of 1,2-bis[N-(Na?2-alkylimidazolium)]ethane bis(hexafluorophosphate)s allows good stacking structure in the crystals. ? 2010 American Chemical Society.

Thermo-solvatochromism in binary mixtures of water and ionic liquids: On the relative importance of solvophobic interactions

The thermo-solvatochromism of 2,6-dibromo-4-[(E)-2-(1-methylpyridinium-4- yl)ethenyl] phenolate, MePMBr2, has been studied in mixtures of water, W, with ionic liquids, ILs, in the temperature range of 10 to 60 °C, where feasible. The objectives of the study were to test the applicability of a recently introduced solvation model, and to assess the relative importance of solute-solvent solvophobic interactions. The ILs were 1-allyl-3-alkylimidazolium chlorides, where the alkyl groups are methyl, 1-butyl, and 1-hexyl, respectively. The equilibrium constants for the interaction of W and the ILs were calculated from density data; they were found to be linearly dependent on NC, the number of carbon atoms of the alkyl group; van't Hoff equation (log K versus 1/T) applied satisfactorily. Plots of the empirical solvent polarities, ET (MePMBr2) in kcal mol-1, versus the mole fraction of water in the binary mixture, χw, showed non-linear, i.e., non-ideal behavior. The dependence of ET (MePMBr2) on χw, has been conveniently quantified in terms of solvation by W, IL, and the "complex" solvent IL-W. The non-ideal behavior is due to preferential solvation by the IL and, more efficiently, by IL-W. The deviation from linearity increases as a function of increasing NC of the IL, and is stronger than that observed for solvation of MePMBr2 by aqueous 1-propanol, a solvent whose lipophilicity is 12.8 to 52.1 times larger than those of the ILs investigated. The dependence on NC is attributed to solute-solvent solvophobic interactions, whose relative contribution to solvation are presumably greater than that in mixtures of water and 1-propanol.

Preparation method of nitrogen-alkyl (deuterated alkyl) aromatic heterocycle and alkyl (deuterated alkyl) aryl ether compound

The invention provides a method for preparing nitrogen-alkyl(deuterated alkyl)aromatic heterocycle and alkyl(deuterated alkyl)aryl ether compounds. The method adopted in the invention specifically comprises the following steps: firstly, adding an alkoxy base (MOR') or a combination reagent Q (comprising a base M'X, an alcohol C and a molecular sieve E) into a solvent B to be stirred; then, addingan aromatic compound D of nitrogen sulfonyl or oxygen sulfonyl into a mixture; separating and purifying after reaction to obtain nitrogen-alkyl(deuterated alkyl)aromatic heterocycle or alkyl(deuterated alkyl)aryl ether. The method can realize one-step conversion from an electron withdrawing benzenesulfonyl protecting group on a nitrogen or oxygen atom to an electron donating alkyl protecting group, avoids using highly toxic alkyl halide, and has advantages of being efficient, economical, environmentally friendly, mild in condition, good in substrate universality and high in yield; the prepareddeuterated compounds can be widely applied to the fields of pharmaceutical chemistry and organic chemistry synthesis.

A Remarkable Fluorescence Quenching Based Amplification in ATP Detection through Signal Transduction in Self-Assembled Multivalent Aggregates

Signal transduction is essential for the survival of living organisms, because it allows them to respond to the changes in external environments. In artificial systems, signal transduction has been exploited for the highly sensitive detection of analytes. Herein, a remarkable signal transduction, upon ATP binding, in the multivalent fibrillar nanoaggregates of anthracene conjugated imidazolium receptors is reported. The aggregates of one particular amphiphilic receptor sensed ATP in high pm concentrations with one ATP molecule essentially quenching the emission of thousands of receptors. A cooperative merging of the multivalent binding and signal transduction led to this superquenching and translated to an outstanding enhancement of more than a millionfold in the sensitivity of ATP detection by the nanoaggregates; in comparison to the “molecular” imidazolium receptors. Furthermore, an exceptional selectivity to ATP over other nucleotides was demonstrated.

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.

Detosylative (Deutero)alkylation of Indoles and Phenols with (Deutero)alkoxides

An efficient strategy for N/O-(deutero)alkylation of indoles and phenols with alkoxides/alcohols as the alkylation reagents is described. The consecutive detosylation/alkylation transformations feature mild reaction conditions, high ipso-selectivity, and good functional group tolerance (>50 examples). A one-pot selective N-alkylation of unprotected indoles with alcohols and TsCl is also realized. The application of this method is demonstrated by the introduction of isotope-labeled (CD3 and 13CH3) groups using the readily accessible labeled alcohols and the synthesis of pharmaceuticals.

Highly-efficient N-arylation of imidazole catalyzed by Cu(II) complexes with quaternary ammonium-functionalized 2-acetylpyridine acylhydrazone

The reaction of (E)-N,N,N-trimethyl-2-oxo-2-(2-(1-(pyridin-2-yl)ethylidene)hydrazinyl)ethan-1-aminium-chloride (HLCl) with copper(II) perchlorate led to mononuclear [CuLCl]ClO4 complex (1). The same reaction with excess of sodium azide gives di

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.

Halogen-bond driven self-assembly of triangular macrocycles

2-Iodoethynylpyridine and 2-iodoethynyl-1-methyl-imidazole self-assemble under halogen-bonding control into discrete macrocycles, viz. supramolecular triangles.