21252-69-7

Basic information

• Product Name: 1-OCTYLIMIDAZOLE
• Synonyms: 1-OCTYLIMIDAZOLE;n-octylimidazole;OIM
• CAS NO: 21252-69-7
• Molecular Formula: C₁₁H₂₀N₂
• Molecular Weight: 180.29
• Mol File: 21252-69-7.mol
• Article Data: 47

Chemical Properties

• Boiling Point: 302.4 °C at 760 mmHg
• Flash Point: 136.7 °C
• Appearance: /
• Density: 0.91 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.00178mmHg at 25°C
• Refractive Index: n20/D1.475
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 7.09±0.10(Predicted)
• BRN: 122643
• CAS DataBase Reference: 1-OCTYLIMIDAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-OCTYLIMIDAZOLE(21252-69-7)
• EPA Substance Registry System: 1-OCTYLIMIDAZOLE(21252-69-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 21252-69-7(Hazardous Substances Data)

Usage

General Description

1-Octylimidazole is a widely used chemical compound with the molecular formula C12H21N2. It appears as a light yellow to brown clear liquid with a low melting and boiling point. 1-OCTYLIMIDAZOLE is primarily known for its role in chemical synthesis, particularly as a catalyst. Its solubility properties make it ideal for use in the manufacture of a variety of products ranging from pharmaceuticals to plastics. It is known for being stable under normal temperatures and pressures, however, it may pose certain health risks including skin and eye irritation or damage to organs through prolonged or repeated exposure.

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

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

Relevant articles and documents

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.

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.

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.

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).

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.

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.

Structured semifluorinated polymer ionic liquids for metal nanoparticle preparation and dispersion in fluorous compartments

Structured semifluorinated polymer ionic liquids (FPILs) contain a flexible hyperbranched polyether core connected with a covalently attached shell of imidazolium cations and perfluorinated alkyl chains at their periphery. In a facile synthesis, alkylatio

Exploring the cellular uptake and localisation of phosphorescent rhenium: Fac -tricarbonyl metallosurfactants as a function of lipophilicity

A systematic study of the cellular uptake of emissive complexes as a function of their lipophilicity is presented. Here a series of amphiphilic rhenium fac-tricarbonyl bisimine complexes bearing axial substituted imidazole or thiazole ligands, [Re(bpy)(CO)3(ImCnHm)]+ {n = 1 m = 3 (1+), n = 4 m = 9 (2+), n = 8 m = 17 (3+), n = 12 m = 25 (4+), n = 16 m = 33 (5+), n = 2 m = 3 (6+); bpy = 2,2′-bipyridine, Im = imidazole} and [Re(bpy)(CO)3(L)]+ {L = 1-mesitylimidazole, ImMes (7+), 4,5-dimethylthiazole, dmt (8+) and 4-methyl-5-thiazole-ethanol, mte (9+)} is reported. The X-ray crystal structures of 2+, 8+ and 9+ confirm the geometry and expected distribution of ligands and indicated that the plane of the imidazole/thiazole ring is approximately parallel to the long axis of the bipy ligand. Luminescence studies revealed excellent properties for their use in cell imaging with visible excitation and broad emission profiles. Their uptake in two distinct species has been examined by fluorescence imaging of the diplomonad fish parasite Spironucleus vortens (S. vortens) and rod-shaped yeast Schizosaccharomyces pombe (Schiz. pombe) as a function of their lipophilicity. The uptake of the complexes was highest for the more lipophilic 2+-5+ in both S. vortens and Schiz. pombe in which the long alkyl chain aids in crossing bilipid membranes. However, the increased lipophilicity of longer chains also resulted in greater toxicity. Localisation over the whole cell varied with differing alkyl chain lengths with complex 2+ preferentially locating to the nucleus of S. vortens, 3+ showing enhanced nuclear partitioning in Schiz. pombe, and 4+ for the remaining cell wall bound in the case of S. vortens. Interestingly, complexes of intermediate lipophilicity such as 7+ and 8+ showed reasonable uptake, proved to be non-toxic, and were capable of crossing exterior cell walls and localising in the organelles of the cells.

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.

Cell Permeable Imidazole-Desferrioxamine Conjugates: Synthesis and in Vitro Evaluation

Desferrioxamine (DFO), a clinically approved iron chelator used for iron overload, is unable to chelate labile plasma iron (LPI) because of its limited cell permeability. Herein, alkyl chain modified imidazolium cations with varied hydrophobicities have been conjugated with DFO. The iron binding abilities and the antioxidant properties of the conjugates were found to be similar to DFO. The degree of cellular internalization was much higher in the octyl-imidazolium-DFO conjugate (IV) compared with DFO, and IV was able to chelate LPI in vitro. This opens up a new avenue in using N-alkyl imidazolium salts as a delivery vector for hydrophilic cell-impermeable drugs.