35203-44-2

Usage

Uses

Used in Pharmaceutical Industry:
1-Propyl-1H-imidazole is used as a chemical intermediate for the production of various pharmaceuticals. Its ability to form stable complexes with metal ions makes it a valuable component in the synthesis of drugs with specific therapeutic properties.
Used in Pesticide Industry:
In the pesticide industry, 1-Propyl-1H-imidazole serves as a chemical intermediate, contributing to the development of effective and safe pesticides. Its stability and complex-forming ability enhance the performance and selectivity of these agrochemicals.
Used in Specialty Chemicals Production:
1-Propyl-1H-imidazole is utilized as a chemical intermediate in the production of specialty chemicals, which are used in various applications such as coatings, adhesives, and sealants. Its thermal stability and complex-forming properties contribute to the performance and durability of these specialty chemicals.
Used as a Corrosion Inhibitor:
1-Propyl-1H-imidazole is used as a corrosion inhibitor, protecting metal surfaces from degradation and extending the service life of equipment and structures. Its ability to form stable complexes with metal ions helps in providing a protective barrier against corrosive agents.
Used as a Stabilizer in Metalworking Fluids:
In the metalworking industry, 1-Propyl-1H-imidazole is used as a stabilizer in metalworking fluids. Its thermal stability and complex-forming ability help maintain the fluid's performance and prevent degradation during high-temperature operations.
Used as a Catalyst in Synthetic Organic Chemistry:
1-Propyl-1H-imidazole is employed as a catalyst in various synthetic organic chemistry processes. Its ability to form stable complexes with metal ions facilitates the acceleration of chemical reactions, improving the efficiency and selectivity of the synthesis.
Used in Energy Storage and Conversion Devices:
1-Propyl-1H-imidazole has potential applications in energy storage and conversion devices, such as lithium-ion batteries and fuel cells. Its thermal stability and complex-forming properties make it a promising component in the development of advanced energy storage materials and systems.

InChI:InChI=1/C6H10N2/c1-6(2)8-4-3-7-5-8/h3-6H,1-2H3

Upstream product

• 288-32-4 1H-imidazole 
• 106-94-5 propyl bromide 
• 65039-16-9 1-butyl-3-propyl-imidazolium; iodide 
• 119171-18-5 1-propyl-3-methyl-1H-imidazol-3-ium iodide 
• 5587-42-8 imidazolyl sodium 
• 107-08-4 1-iodo-propane 
• 31410-01-2 1-allylimidazole 
• 5036-48-6 3-(1H-imidazol-1-yl)propan-1-amine 
• 540-54-5 1-Chloropropane 

Downstream Products

• 119171-18-5 1-propyl-3-methyl-1H-imidazol-3-ium iodide 
• 103815-48-1 1-(2-Oxo-2-phenyl-ethyl)-3-propyl-3H-imidazol-1-ium; bromide 
• 1094598-64-7 3-(3-{[1-phenyl-meth-(E)-ylidene]-amino}-propyl)-1-propyl-3H-imidazol-1-ium bromide 
• 1361182-29-7 1-propylimidazolium picrate 

Relevant academic research and scientific papers

On the mesophase formation of 1,3-dialkylimidazolium ionic liquids

A series of seven different 1,3-dialkylimidazolium-based ion-pair salts with the same molecular weight and size but different symmetries was synthesized. For all salts, bromide was chosen as the counterion, giving the series ([CnIMCm][Br]), where IM = imidazolium and Cn and Cm are varying N-alkyl substituents with n + m = 13. Thus, the effect of symmetry on the physicochemical properties, such as thermal transitions, densities and viscosities and particularly mesophase formation, is investigated herein. All salts are fully characterized by NMR spectroscopy and mass spectrometry, and their physicochemical properties such as thermal transitions, densities, and viscosities are reported. Single crystal X-ray structure analysis is reported for 1-tridecylimidazolium bromide ([C0IMC13][Br]) and 1-ethyl-3- undecylimidazolium bromide ([C2IMC11][Br]). Salts 1-tridecylimidazolium bromide ([C0IMC13][Br]) and 1-dodecyl-3-methylimidazolium bromide ([C1IMC12][Br]) exhibit thermotropic liquid crystal behavior, confirmed by differential scanning calorimetry, polarized optical microscopy, and small-angle X-ray diffraction to be the SmA mesophase. A structure with interdigitation of alkyl chains is observed for all of [C0IMC13][Br], [C1IMC12][Br], and [C2IMC11][Br], despite the absence of thermotropic liquid crystalline behavior for the latter (and all other isomers with an alkyl chain length less than 12 carbon atoms). This allows us to draw the conclusion that for the liquid crystal phase of an ionic liquid to exist, not only are the calamitic shape and integral length of a molecule important but a minimal alkyl chain length of n = 12 is also required. Therefore, a dodecyl group could be considered as the functional group responsible for liquid crystalline behavior.

Convenient synthesis of imidazolium based dicationic ionic liquids

A series of imidazolium based Dicationic Ionic Liquids (ILs) have been prepared and characterized successfully. Derivatives are prepared keeping the alkyl chain of alkylimidazole as methyl, ethyl, and propyl groups and the linker dibromoalkane is varied as an ethyl, propyl and butyl group. The variations of anions like Br?, BF4 ? and PF6 ? impact their morphological appearance like amorphous powder to low melting white solids or a hygroscopic nature. Refluxing the alkylimidazoles and dibromoalkanes in toluene for 24?h and an easy workup procedure makes this methodology more time saving for detailed exploration of Dicationic ILs. The formation of dicationic ILs with their anions like Br?, BF4 ?, PF6 ? has been confirmed with 1H, 13C, 31P and 19F NMR spectroscopy as well as the High Resolution Mass Spectroscopy Electron Impact technique.

In-situ synthesis of mercury(II)-N-heterocyclic carbene complexes by using “oxide route”, structural characterization and their photo-catalytic degradation activity for dyes

N-alkylated imidazole derivatives (1a-1b), mono-azolium salts (SL2-SL3) and their symmetrically (SC2) and non-symmetrically (SC3) substituted mercury(II)-N-heterocyclic carbene (Hg(II)-NHC) complexes were synthesized by using “oxide route”. The characterization was done by using physical (i.e., solubility, melting point determination, compound microscopic analysis) and spectral (i.e., UV-Visible spectroscopy, FT-IR spectroscopy, 1H and 13C NMR spectroscopy) methods. Chemical equilibrium between monomeric and dimeric structures of bromide-bridging Hg(II)-NHC complexes was also observed in the presence of solvent. Photo-catalytic degradation rate of two environmentally polluting dyes i.e., methylene blue (MR) and congo red (CR), was investigated by using compound 1 (SC2) and compound 2 (SC3) which demonstrated that the compound 2 had maximum degradation rate in the range of 70–80% as compared to the compound 1 (60–70% ).

Direct Deamination of Primary Amines via Isodiazene Intermediates

We report here a reaction that selectively deaminates primary amines and anilines under mild conditions and with remarkable functional group tolerance including a range of pharmaceutical compounds, amino acids, amino sugars, and natural products. An anomeric amide reagent is uniquely capable of facilitating the reaction through the intermediacy of an unprecedented monosubstituted isodiazene intermediate. In addition to dramatically simplifying deamination compared to existing protocols, our approach enables strategic applications of iminium and amine-directed chemistries as traceless methods. Mechanistic and computational studies support the intermedicacy of a primary isodiazene which exhibits an unexpected divergence from previously studied secondary isodiazenes, leading to cage-escaping, free radical species that engage in a chain, hydrogen-atom transfer process involving aliphatic and diazenyl radical intermediates.

On the effects of head-group volume on the adsorption and aggregation of 1-(n-hexadecyl)-3-Cm-imidazolium bromide and chloride surfactants in aqueous solutions

The effects of the length of alkyl side chain (Cm) of ionic liquid-based surfactants (ILBSs) on their adsorption at the water/air interface, and aggregation in aqueous solutions were investigated for the series 1-(n-hexadecyl)-3-Cm-imidazolium bromides and chlorides, where Cm = C1-C4 for the bromides, and C1-C5 for the chlorides. These physicochemical properties were calculated from surface tension, conductivity, and fluorescence data. It was found that increasing the length of Cm (i.e., volume of the head group) leads to enhancement of surface activity, increase in the area per surfactant molecule at the water/air interface (Amin) and the degree of counter-ion dissociation (αmic). Our data also indicated that increasing the volume of the head group results in a decrease of the critical micelle concentration (cmc), Gibb's free energy of adsorption and micellization, and microscopic polarity of interfacial water. In order to delineate the effects of the presence of unsaturation in the HG, we included members that carry Cm = vinyl and allyl in the bromide series. The effect of these groups was found to be similar to removing a methylene group from Cm. The dependence of the solubilization of a lipophilic dye (Sudan IV) and a drug (nitrendipine) on the length of Cm was also studied.

Continuous production process of 2, 3, 5-trichloropyridine

According to a continuous production process of 2, 3, 5-trichloropyridine, a continuous tubular chlorinator is adopted, pyridine is taken as a starting raw material, chlorination reaction is continuously carried out step by step by virtue of a catalyst 1 and a catalyst 2 which are independently researched and developed, and 2, 5-dichloropyridine and 2, 3, 5-trichloropyridine are prepared in sequence. In the preparation process of a catalyst 1 and a catalyst 2, the mass ratio of 1-chloropropane to imidazole to 2-chloroethyl diphenylphosphine to nickel tetracarbonyl is 1.2: 1: 3.7: 2.5, and the mass ratio of 1-chloropropane to imidazole to 2-chloroethyl diphenylphosphine to sodium hexachlororhodate hydrate is 1.2: 1: 3.7: 15. By means of the continuous tubular chlorinator, cheap and easily available pyridine is used as a starting raw material, chlorine atoms are introduced step by step through catalytic chlorination, the atom economy is good, the reaction selectivity is good, the yield of 2, 3, 5-trichloropyridine can be stabilized at 80% or above, the production efficiency is high, the process is easy to control, and the method is environmentally friendly and suitable for industrial production.

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.

CYCLIC AMINE DERIVATIVE AND PHARMACEUTICAL USE THEREOF

An object of the present invention is to provide a compound exerting an analgesic effect against pain, in particular, neuropathic pain and/or fibromyalgia syndrome. The present invention provides a cyclic amine derivative represented by the following general formula, or a pharmacologically acceptable salt thereof.

Novel imidazole aldoximes with broad-spectrum antimicrobial potency against multidrug resistant gram-negative bacteria

In the search for a new class of potential antimicrobial agents, five novel N-substituted imidazole 2-aldoximes and their six quaternary salts were evaluated. The antimicrobial activity was assessed against a panel of representative Gram-positive and Gram-negative bacteria, including multidrug resistant bacteria. All compounds demonstrated potent in vitro activity against the tested microorganisms, with MIC values ranging from 6.25 to 50.0 μg/mL. Among the tested compounds, two quaternary compounds (N-but-3-enyl- and meta- (10) or para- N-chlorobenzyl (11) imidazolium 2-aldoximes) displayed the most potent and broad-spectrum activity against both Gram-positive and Gram-negative bacterial strains. The broth microdilution assay was also used to investigate the antiresistance efficacy of the both most active compounds against a set of Enterobacteriaceae isolates carried a multiple extended-spectrum β-lactamases (ESBLs) in comparison to eight clinically relevant antibiotics. N-but-3-enyl-N-meta-chlorobenzyl imidazolium 2-aldoxime was found to possess promising antiresistance efficacy against a wide range of β-lactamases producing strains (MIC 2.0 to 16.0 μg/mL). Best results for that compound were obtained against Escherichia coli and Enterobacter cloacae producing multiple β-lactamases form A and C molecular classes, which were 32- and 128-fold more potent than ceftazidime and cefotaxime, respectively. To visualize the results, principal component analysis was used as an additional classification tool. The mixture of ceftazidime and compound 10 (3 μg:2 μg) showed a strong activity and lower the necessary amount (up to 40-fold) of 10 against five of ESBL-producing isolates (MIC ≤ 1 μg/mL).

A planar anthracene–imidazolium/anthracene–benzimidazolium cation system in a spherical polyoxometalate matrix: Synthesis, crystallography and spectroscopy

A series of ion–pair compounds, comprising of Lindqvist type isopolyanions viz., [Mo6O19]2?and [W6O19]2?as the counter anions and anthracene–imidazolium/anthracene–benzimidazolium as counter cations, have been described. Structures of the isolated stoichiometric solids have been unambiguously determined by single crystal X-ray diffraction analysis. In spite of the structural incompatibility between anthracene (planar) and the present polyoxometalate anions (spherical), coulombic and several intermolecular weak interactions, e.g. C–H?O, C–H?π, π–π, etc. compensate the destabilization energy raised due to presence of the structurally mis-matched components in the respective crystal lattices. Single-crystal- as well as powder X-ray-diffraction (PXRD) analyses reveal iso-structural relationship between the hexamolybdates- and hexatungstates-associated ion pair compounds. Conformational variation has been observed in the crystal structures containing benzyl benzimidazolium counter cations. Diffuse reflectance electronic absorption spectral studies are performed to understand the relatively intense color of the title compounds in their solid states in comparison to their respective solution states.