53657-09-3

Basic information

• Product Name: 1-heptyliMidazole
• Synonyms: 1-heptyliMidazole;1-Heptyl-1H-imidazole
• CAS NO: 53657-09-3
• Molecular Formula: C₁₀H₁₈N₂
• Molecular Weight: 166.26332
• Mol File: 53657-09-3.mol

Chemical Properties

• Boiling Point: 286.2°C at 760 mmHg
• Flash Point: 126.9°C
• Appearance: /
• Density: 0.92g/cm³
• Vapor Pressure: 0.0046mmHg at 25°C
• Refractive Index: 1.5
• CAS DataBase Reference: 1-heptyliMidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 1-heptyliMidazole(53657-09-3)
• EPA Substance Registry System: 1-heptyliMidazole(53657-09-3)

Safety Data

• Hazardous Substances Data: 53657-09-3(Hazardous Substances Data)

Usage

Uses

Used in Corrosion Inhibition:
1-heptylImidazole serves as a corrosion inhibitor, protecting metals from degradation and extending their service life. Its ability to form a protective film on metal surfaces makes it an effective agent in preventing corrosion.
Used in Catalyst Production:
As a catalyst, 1-heptylImidazole accelerates chemical reactions, improving efficiency and reducing the energy and time required for various industrial processes.
Used in Pharmaceutical Industry:
1-heptylImidazole is utilized in the production of pharmaceuticals, where its unique chemical structure contributes to the development of new drugs and therapeutic agents.
Used in Agricultural Chemicals:
In the agricultural sector, 1-heptylImidazole is employed in the creation of agricultural chemicals, such as pesticides and fertilizers, to enhance crop protection and yield.
Used as a Polymer Stabilizer:
1-heptylImidazole acts as a stabilizer in polymers, enhancing their resistance to degradation and improving their overall performance in various applications.
Used in Lubricants and Greases:
As a component in lubricants and greases, 1-heptylImidazole reduces friction and wear, contributing to the longevity and efficiency of mechanical systems.
Used as Antifungal and Antibacterial Agent:
1-heptylImidazole has demonstrated potential as an antifungal and antibacterial agent, making it useful in applications requiring the control of microbial growth, such as in medical and hygiene products.

InChI:InChI=1/C10H18N2/c1-2-3-4-5-6-8-12-9-7-11-10-12/h7,9-10H,2-6,8H2,1H3

Upstream product

• 288-32-4 1H-imidazole 
• 629-06-1 1-Chloroheptane 
• 629-04-9 1-Bromoheptane 
• 5587-42-8 imidazolyl sodium 
• 111-83-1 1-bromo-octane 

Downstream Products

• 97163-28-5 1-heptyl-3-[2-[4-[(methanesulfonyl)amino]phenyl]-2-oxoethyl]imidazolium bromide 
• 97142-73-9 1-[3-((2,6-dimethylphenyl)sulfamoyl)propyl]-3-heptylimidazolium chloride 
• 97142-69-3 1-[4-(4-Fluorophenyl)-4-oxobutyl]-3-heptylimidazolium bromide 
• 97142-75-1 1-heptyl-3-(4-phenylbutyl)imidazolium chloride 
• 97142-68-2 1-Heptyl-3-[3-(4-methoxyphenyl)propyl]imidazolium bromide 
• 97163-73-0 1-[4-[4-(Acetylamino)phenyl]butyl]-3-heptylimidazolium 4-methylbenzenesulfonate 
• 97142-70-6 1-Heptyl-3-[4-(4-methoxyphenyl)butyl]imidazolium bromide 
• 97142-64-8 1-[4-(4-chlorophenyl)butyl]-3-heptylimidazolium chloride 

Relevant articles and documents

Bilateral asymmetric alkyl imidazole ionic liquid, preparation method and applications thereof

The invention discloses a bilateral asymmetric alkyl imidazole ionic liquid, a preparation method and applications thereof. The bilateral asymmetric alkyl imidazole ionic liquid has a structural formula defined in the specification, wherein X comprises bis(2-ethylhexyl) phosphate anions, bis(trifluoromethanesulfonyl imide) anions, hexafluorophosphate radicals, thiocyanate radicals, trifluoroacetate radicals or dicyandiamide radicals. According to the invention, a series of bilateral asymmetric alkyl imidazole ionic liquids with novel structures are synthesized from imidazole monomers, so that the types of the imidazole ionic liquids are enriched; and the obtained bilateral asymmetric alkyl imidazole ionic liquid as a lubricating additive has obvious antifriction and anti-wear effects, and the physical state change, the solubility, the thermal stability, the antifriction and anti-wear properties and the like of the ionic liquid can be regulated and controlled by regulating the anionstructure of the ionic liquid, so that the ionic liquid has wide application prospect.

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.

Liquid Nickel Salts: Synthesis, Crystal Structure Determination, and Electrochemical Synthesis of Nickel Nanoparticles

New nickel-containing ionic liquids were synthesized, characterized and their electrochemistry was investigated. In addition, a mechanism for the electrochemical synthesis of nanoparticles from these compounds is proposed. In these so-called liquid metal salts, the nickel(II) cation is octahedrally coordinated by six N-alkylimidazole ligands. The different counter anions that were used are bis(trifluoromethanesulfonyl)imide (Tf2N-), trifluoromethanesulfonate (OTf-) and methanesulfonate (OMs-). Several different N-alkylimidazoles were considered, with the alkyl sidechain ranging in length from methyl to dodecyl. The newly synthesized liquid metal salts were characterized by CHN analysis, FTIR, DSC, TGA and viscosity measurements. An odd-even effect was observed for the melting temperatures and viscosities of the ionic liquids, with the complexes with an even number of carbon atoms in the alkyl chain of the imidazole having a higher melting temperature and a lower viscosity than the complexes with an odd number of carbons. The crystal structures of several of the nickel(II) complexes that are not liquid at room temperature were determined. The electrochemistry of the compounds with the lowest viscosities was investigated. The nickel(II) cation could be reduced but surprisingly no nickel deposits were obtained on the electrode. Instead, nickel nanoparticles were formed at 100 % selectivity, as confirmed by TEM. The magnetic properties of these nanoparticles were investigated by SQUID measurements.

Iron(II) spin-crossover complexes with Schiff base like ligands and N-alkylimidazoles

Three new iron(II) spin-crossover complexes with N2O2-coordinating Schiff base like equatorial ligands and alkylimidazole ligands in the axial positions were synthesised. The chain length of the alkylimidazole was varied from the previously published 1 to 5, 7 and 10 carbon atoms to investigate the influence of the alkyl chain length on the spin-transition behaviour in solution and in the solid state. The crystal structures of [1(HeptIm)2] and [1(DecIm)2] (1 = Fe complex with equatorial Schiff base like ligand; HeptIm = N-heptylimidazole, DecIm = N-decylimidazole) and the packing of the molecules in the crystals are discussed.

Antimicrobial activity and SAR study of new gemini imidazolium-based chlorides

A series of 70 new 3,3′(α,ω-dioxaalkyl)bis(1- alkylimidazolium) chlorides were synthesized. They were characterized with respect to surface active properties and antimicrobial activity against the following pathogens: Staphylococcus aureus, Enterococcus faecalis, Acinetobacter baumannii, Escherichia coli, Klebsiella pneumoniae, Enterobacter cloacae, Pseudomonas aeruginosa, Candida krusei, and Candida albicans. In this article, besides description of the synthesis, we characterize a set of features of these compounds, concerning their structure (described by the length of the dioxaalkan spacer and the length of the alkyl substituent in the aromatic ring) and surface active properties (critical micelle concentration, value of surface tension at critical micelle concentration, value of surface excess, molecular area of a single particle, and free energy of adsorption of molecule). Then, we present a SAR study for Staphylococcus aureus, as one of the most widespread pathogenic strains, conducted with the help of the Dominance-based Rough Set Approach (DRSA), that involves identification of relevant features and relevant combinations of features being in strong relationship with a high antimicrobial activity of the compounds. The SAR study shows, moreover, that the antimicrobial activity is dependent on the type of substituents and their position at the chloride moiety, as well as on the surface active properties of the compounds.

Chemo-immunotherapeutic antimalarials targeting isoprenoid biosynthesis

We synthesized 30 lipophilic bisphosphonates and tested them in malaria parasite killing (targeting parasite geranylgeranyl diphosphate synthase, GGPPS) and human γδ T cell activation (targeting human farnesyl diphosphate synthase, FPPS). Similar patterns of activity were seen in inhibiting human FPPS and Plasmodium GGPPS, with short to medium chain-length species having most activity. In cells, shorter chain-length species had low activity, due to poor membrane permeability, and longer chain length species were poor enzyme inhibitors. Optimal activity was thus seen with ～C 10 side-chains, which have the best combination of enzyme inhibition and cell penetration. We also solved the crystal structure of one potent inhibitor, bound to FPPS. The results are of interest since they suggest the possibility of a combined chemo/immuno-therapeutic approach to antimalarial development in which both direct parasite killing and γδ T cell activation can be achieved with a single compound.

Symmetrical 1, 3-Dialkylimidazolium Based Ionic Liquid Crystals

The synthesis and characterization for a series of symmetrical 1, 3-dialkylimidazolium salts with different chain lengths and counter anions together with their 1-alkylimidazole precursors are described. Liquid crystal (LC) properties of these salts are studied. Images under polarizing optical microscopy show focal conic texture together with homeotropic domains. A smectic A mesophase, typical for rod-like imida-zolium salts, is assigned. Studies from powder X-ray diffraction suggest a lamellar structure with non-interdigitated monolayer arrangement for the LC salts in the mesophase. In addition, a short note on the structure and property relationship for rod-like, discor fan-like, and dendritic shaped imidazolium ionic liquid crystals (ImILCs) forming smectic, columnar, and cubic phase is briefly summarized. Acomparison of minimum alkyl chain length needed for 1-alkyl-3-methyl and symmetrical 1, 3-dialkyl ImILCs to exhibit LC behavior is addressed.

β-Carotene: A green, inexpensive, and convenient solvatochromic probe for the determination of solvent polarizability

Solvent polarizability has been previously determined by using the solvatochromic probe 3,20-di-tert-butyl-2,2,21,21-tetramethyl-3,5,7,9,11,13,15, 17,19-docosanonaene whose synthesis involves 15 steps. We show here that the natural dye β-carotene, 1,1′-(3,7,12,16-tetramethyl-1,3,5,7,9,11,13, 15,17-octadecanonaene-1,18-diyl)bis[2,6,6-trimethylcyclohexene], can be conveniently employed for the accurate determination of the same solvent property. This conclusion is based on both theoretical calculations and experimental data. The former includes free energies of solvation, and the wavenumber of the longest wavelength (i.e., the solvatochromic) transition. Both quantities for β-carotene correlate linearly with the corresponding values of the docosanonaene, with slopes and correlation coefficients of practically unity. The plot of experimentally calculated solvent polarizability of β-carotene versus that of the docosanonaene was found to be linear for 68 solvents. Previously unknown solvent polarizability values are reported for eight ROCH2CH2OH (R = C1 to C10) and four 1-allyl-3-R-imidazolium chloride ionic liquids (R = C6 to C10). The dependence of solvent polarizability on the number of carbon atoms in the hydrocarbon chains of several classes of solvents is calculated, it shows the importance of van der Waals interactions in ionic liquids.

1,2-Bis[N-(N′-alkylimidazolium)]ethane salts: A new class of organic ionic plastic crystals

A new class of organic ionic plastic crystals was discovered. A series of alkylene 1,2-bis[N-(N′-alkylimidazolium)] salts with Br- and PF6- anions was prepared and most of the ethylene (C 2) linked compounds undergo multiple solid-solid phase transitions as determined by differential scanning calorimetry (DSC). The salts with longer spacers (C3 or C4) between the imidazolium units do not display any solid-solid transitions. The PF6- salts with terminal C10 and C12n-alkyl moieties are "classical" organic ionic plastic crystals by Timmermans' definition; they have low ΔSf (11 J K-1 mol-1 for C10 and 12 J K-1 mol-1 for C12). Additionally, the C2 linked bis-imidazolium salts with n-butyl, n-hexyl, n-heptyl and n-octyl termini all undergo two, three or four solid state transitions and exhibit ΔSf values in the range of 36-49 J K-1 mol-1, which are similar to those of other known ionic plastic crystalline materials. These materials were additionally characterized via ionic conductivity and solid state NMR. These ionic plastic crystals are presumably single-ion conductors, but the ionic conductivities appear to be too low for practical applications. The activation energy for conduction decreases as these compounds are heated through each solid-solid transition. The lack of any change in solid state 2H NMR spectra with temperature indicates that there is no change in phenyl ring flipping, suggesting no change in the imidazolium local environment. A resolution of this apparent dichotomy is perhaps that the counterions reside with the ethylene spacers between imidazolium moieties.

Synthesis and properties of chiral imidazolium ionic liquids with a (1R,2S,5R)-(-)-menthoxymethyl substituent

A series of 1-[(1R,2S,5R)-(-)-menthoxymethyl]-3-alkylimidazolium salts have been synthesized, producing both hydrophilic and hydrophobic chiral imidazolium ionic liquids. Their physicochemical properties, single-crystal X-ray structures, antimicrobial activities, and antielectrostatic effects were determined and these compounds have proven to represent not only potential new solvents in asymmetric synthesis, but also effective, disinfectants with antielectrostatic activity. Given the number and diversities of the possible conformations and interionic interactions, coupled with the chiral nature of the cations, it should come as no surprise that these salts exhibit ionic liquid behavior and are so difficult to crystallize. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.