4238-71-5

Basic information

• Product Name: N-Benzylimidazole
• Synonyms: RARECHEM AQ NN 0036;TIMTEC-BB SBB003990;Imidazole, 1-benzyl-;N-Benzylimidazole;1-(PHENYLMETHYL)-1H-IMIDAZOLE;1-BENZYLIMIDAZOLE;1-BENZYL-1H-IMIDAZOLE;AKOS BBS-00000222
• CAS NO: 4238-71-5
• Molecular Formula: C₁₀H₁₀N₂
• Molecular Weight: 158.2
• EINECS: 224-200-4
• Product Categories: Imidazoles;Heterocyclic Compounds;Building Blocks;Heterocyclic Building Blocks;Building Blocks;C9 to C30+;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 4238-71-5.mol

Chemical Properties

• Melting Point: 68-70 °C(lit.)
• Boiling Point: 310 °C(lit.)
• Flash Point: 141.3 °C
• Appearance: Brownish/Crystals
• Density: 1.2419 (rough estimate)
• Vapor Pressure: 0.00112mmHg at 25°C
• Refractive Index: 1.6392 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 6.79±0.10(Predicted)
• Water Solubility: insoluble
• BRN: 114571
• CAS DataBase Reference: N-Benzylimidazole(CAS DataBase Reference)
• NIST Chemistry Reference: N-Benzylimidazole(4238-71-5)
• EPA Substance Registry System: N-Benzylimidazole(4238-71-5)

Safety Data

• Statements: 36/37/38
• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 10
• Hazardous Substances Data: 4238-71-5(Hazardous Substances Data)

Usage

Uses

1-Benzylimidazole is used as an inducer for various cytochrome P-450 isozymes and as an inhibitor of thromboxane A2 synthase for [application reason] in the pharmaceutical industry. This dual functionality allows it to play a role in the development of drugs targeting specific enzyme pathways.
Used in Pharmaceutical Industry:
1-Benzylimidazole is used as a key compound in the preparation of cyclodextrin-ionic liquid polymer (βCD-BIMOTs-TDI) for [application reason] in drug formulation and delivery. The cyclodextrin-ionic liquid polymer can enhance the solubility, stability, and bioavailability of drugs, making it a valuable tool in the pharmaceutical industry.
Additionally, 1-Benzylimidazole may be involved in the estimation of iodide in pharmaceutical samples using a spectrophotometric method, as it can interact with sodium thiosulfate pentahydrate. This application is particularly useful in quality control and assurance processes within the pharmaceutical industry.

Biochem/physiol Actions

1-Benzylimidazole is a CYP inhibitor that inhibits the biotransformation of MeO-BDEs (methoxylated-brominated diphenyl ethers) to OH-BDEs (hydroxylated) in fishes.

InChI:InChI=1/C10H10N2/c1-2-4-10(5-3-1)8-12-7-6-11-9-12/h1-7,9H,8H2

Upstream product

• 288-32-4 1H-imidazole 
• 100-44-7 benzyl chloride 
• 23269-10-5 1-benzyl-1H-imidazole-2-thione 
• 2466-76-4 N-Acetylimidazole 
• 100-39-0 benzyl bromide 
• 36954-03-7 imidazolide 
• 10364-93-9 1-(4-methoxybenzoyl)-imidazole 
• 584-08-7 potassium carbonate 
• 103-63-9 1-phenyl-2-bromoethane 
• 101853-78-5 1-benzyl-4,5-dibromo-1H-imidazole 
• 106848-38-8 1-benzyl-4-bromo-1H-imidazole 
• 31250-80-3 1-benzyl-2,4,5-tribromo-1H-imidazole 
• 56643-69-7 1-(2-chlorobenzyl)-1H-imidazole 
• 124782-15-6 2,4,6,8,10,12-hexabenzyl-2,4,5,8,10,12-hexaazatetracyclo[5.5.0.0^3,11.0^5,9]dodecane 

Downstream Products

• 327626-37-9 diisopropyl-carbamic acid (1-benzyl-1H-imidazol-2-yl)-phenyl-methyl ester 
• 40229-81-0 2-benzoyl-1-benzyl-imidazole 

Relevant articles and documents

Improved methods for the synthesis and isolation of imidazolium based ionic salts

Solvent-free reactions were used for the synthesis of a series of imidazolium-based ionic salts: 3,3′-[pyridine-2,6-diylbis(methylene)]bis(1-R-1H-imidazol-3-ium)chloride; (R = methyl, ethyl, butyl, isobutyl, hexyl, and benzyl). A simple and effective filtration process was used to isolate all the products in high purity and with yields ≥93% within a 24 h period. The highly pure ionic compounds which are precursors to N-heterocyclic carbene ligands used in catalysis were fully characterized as gray-white hygroscopic salts.

Anti-corrosion properties of new imidazolium-based ionic liquids as a function of cation structure

For perhaps the first time, five imidazolium-based ionic liquids (ILs) were formulated, and their inhibitory effects on 304SS corrosion in 1.0 M HCl solution were explored using chemical and electrochemical procedures. Elemental identification, FT-IR, 13C spectra and 1H NMR analysis were used to verify the molecular structure of the new ILs. These tests showed that at quite small doses, the new ILs are effective inhibitors. The synthesized ILs have overall efficiency ranging from 63 to 95 percent. Ionic liquids' adsorption force is influenced by the organic cation part of their interfacial structure. The data show that ILs (R = –OCH3) has the highest ionic liquid adsorption. The existence of NO2 group in the cationic part of ILs has an adverse influence on ILs adsorption.

Azolium mediated N[sbnd]Heterocyclic carbene selenium adducts: Synthesis, cytotoxicity and molecular docking studies

Ionic liquids (ILs) are remarkable for biological activities in numerous medical fields. With the aim of enhancing biological potential of azolium based ILs, four new selenium-N-Heterocyclic Carbene (Se-NHC) adducts were synthesized from bis-imidazolium and bis-benzimidazolium molten salts. Synthesized ILs (L1-L4) and Se-NHC adducts (C1[sbnd]C4) were confirmed through elemental analysis, chromatographic and spectroscopic techniques including UHPLC-PDA, FTIR, 1H NMR & 13C NMR spectroscopy as well as mass spectrometry. The compounds were found stable in solution form for upto 96 h measured spectroscopically and showed partition coefficient with optimum lipophilicity measured through shake flask method. The simulation studies of these compounds for cancerous proteins indicated that there could be good to high anticancer potential due to their high affinity and less binding energies for COX-1, EGF, VEGF-A and HIF cancer protein targets. The In Vitro cytotoxicity study of compounds confirmed that these compounds were found highly active showeing IC50 against HCT-116 (1.074–1.116 μg mL?1), A549 (0.977–1.325 μg mL?1) and MCF-7 (0.869–1.378 μg mL?1) which is almost better than standard drug 5-Flourouracil but slightly lower than cisplatin and oxaliplatin. The interaction study of compounds with albumin proteins (BSA) and hemolysis assay assured their least toxicity.

Benzimidazole- And Imidazole-Fused Selenazolium and Selenazinium Selenocyanates: Ionic Organoselenium Compounds with Efficient Peroxide Scavenging Activities

Three new classes of ionic organoselenium compounds containing cationic benzimidazolium and imidazolium ring systems with selenocyanates as counterions are described. The cyclization of N,N′-disubstituted benzimidazolium and imidazolium bromides having N-(CH2)2-Br and N-(CH2)3-Br groups in the presence of potassium selenocyanate (KSeCN) led to formation of the corresponding selenazolium selenocyanates (21a, 21b, 22a, and 22b) and selenazinium selenocyanates (21c, 21d, 22c, and 22d). However, the open-chain selenocyanates with additional selenocyanate counterions (21e, 21f, 22e, and 22f) were formed from the N,N′-disubstituted benzimidazolium and imidazolium bromides having N-(CH2)6-Br groups. Mechanistic studies were carried out to understand the feasibility of such cyclization processes in the presence of KSeCN. The compounds were studied further for their potencies to catalytically reduce H2O2 in the presence of thiols. Interestingly, the cyclic selenazolium (21a, 21b, 22a, and 22b) and selenazinium compounds (21c, 21d, 22c, and 22d) exhibited significantly higher antioxidant activities than the corresponding acyclic selenocyanates (21f, 22e, and 22f). Selected compounds (22d and 22e) were further evaluated for their potencies in modulating the intracellular level of reactive oxygen species (ROS) in a representative macrophage cell line (RAW 264.7). Owing to the cationic nature of compounds, they may target and scavenge mitochondrial ROS in the cellular medium.

MICROBICIDE AMMONIUM-IMIDAZOLIUM OLIGOMERS AND THEIR ANTI-FUNGAL COMPOSITIONS

The present disclosure relates to compositions comprising an oligomer of Formula (I): having imidazolium and diammonium substituents; and an anti-fungal compound comprising at least one triazole group, e.g. fluconazole, itraconazole, or voriconazole. The compositions as described herein may be used as an anti-fungal composition for therapeutic and non-therapeutic applications.

Metabolically stable 5-HMF derivatives for the treatment of hypoxia

5-HMF derivative compounds that bind covalently with hemoglobin are provided. Methods of treating sickle cell disease and other hypoxia-related disorders by administering such compounds are also provided.

CHEMOSELECTIVE SENSITIVITY BOOSTER FOR TAGGING A PEPTIDE, PEPTIDE CONJUGATE, OR SIMILAR REACTIVE MOLECULE

The invention pertains to chemoselective sensitivity booster for tagging a peptide, peptide conjugate, or similar reactive molecule for analysis of a peptide, protein, antibody, protein bioconjugate, antibody bioconjugate, and similar analytes. The sensitivity booster comprises of sp2 or sp3 nitrogen centers in combination with hydrophobic carbon chains linked with an electrophile or nucleophile for attachment with a peptide, peptide conjugate, or molecules with similar reactivity.

Imidazo-Fused Isoindoles by Pd(II)/Ag(I)-Promoted Intramolecular Dehydrogenative Coupling

An effective Pd(II)/Ag(I)-promoted intramolecular cross-dehydrogenative coupling (CDC) of substituted 1-benzylimidazoles under air provides, for the first time, a simple access to several functionalized imidazo[2,1-a]isoindoles, an interesting class of polycyclic heteroaromatic compounds. The direct involvement of two unactivated carbon–hydrogen bonds, without any directing group, grants an elevated atom economy of the whole process.

Synthesis and characterization of N-(arylmethylene)-benzimidazole/imidazole-borane compounds

N-(arylmethylene)-benzimidazole/imidazole-borane compounds (7-10) based on ferrocene/benzene were synthesized in a cost-effective way by reacting N-(arylmethylene)-benzimidazole/imidazoles with ammonium sulfate ((NH4)2SO4) and sodium borohydride (NaBH4). The structures of compounds 7-9 were determined by X-ray crystallography. Four compounds displayed high thermal decomposition temperatures (182-256°C) according to the thermogravimetry (TG) measurements. Interestingly, these compounds showed promising applications as potential propellant due to their spontaneous combustion upon contact concentrated HNO3 (≥ 95 %) and catalytic effect on the thermal degradation of ammonium perchlorate (AP).

Synthesis and investigation of inhibitory activities of imidazole derivatives against the metallo-β-lactamase IMP-1

Mutations in bacteria can result in antibiotic resistance due to the overuse or abuse of β-lactam antibiotics. One strategy which bacteria can become resistance toward antibiotics is secreting of metallo β-lactamase enzymes that can open the lactam ring of the β-lactam antibiotic and inactivate them. This issue is a threat for human health and one strategy to overcome this situation is co-administration of β-lactam antibiotics with an inhibitor. So far, no clinically available inhibitors of metallo β-lactamases (MBLs) reported and the clinically inhibitors of serine β-lactamase are useless for MBLs. Accordingly, finding a potent inhibitor of the MBLs being very important. In this study, imidazole derivatives primarily were synthesized and their inhibitory activity were measured. Later in silico binding model was used to predict the configuration and conformation of the ligands into the active site of enzyme. Two molecules demonstrated with IC50 of 39 μM and 46 μM against MBL (IMP-1).