51389-04-9

Usage

Structure

A benzene ring fused to an imidazole ring with a thioether group (S) attached to the imidazole ring and a 2-propenyl group (CH2=CH-CH3) attached to the sulfur atom.

Type

Benzimidazole derivative

Potential applications

Building block in organic synthesis, precursor for pharmaceutical drug development, research and analytical chemistry

Handling precautions

May pose health risks if not properly managed.

Upstream product

• 95-54-5 1,2-diamino-benzene 
• 106-95-6 allyl bromide 
• 134469-07-1 Benzimidazol-2-thiol 
• 89-92-9 2-methylbenzyl bromide 
• 583-39-1 2,3-dihydrobenzimidazol-2-thione 
• 58536-70-2 benzimidazole-2-thione 
• 107-05-1 3-chloroprop-1-ene 

Downstream Products

• 27097-21-8 3-Methyl-2,3-dihydrothiazolo<3,2-a>benzimidazol 
• 245-57-8 4H-benzimidazo[2,1-b][1,3]thiazine 
• 245-58-9 2H-1,3-thiazino<3,2-a>benzimidazole 
• 87216-53-3 3-allylbenzimidazoline-2-thione 
• 134469-07-1 Benzimidazol-2-thiol 
• 50463-17-7 2-(allylthio)benzo[d]oxazole 
• 2179-57-9 diallyl disulphide 
• 124530-69-4 1,2-diallyl sulfanyl-1H-benzoimidazole 

Relevant academic research and scientific papers

Computational, MD simulation, SEM/EDX and experimental studies for understanding adsorption of benzimidazole derivatives as corrosion inhibitors in 1.0 M HCl solution

The adsorption and corrosion inhibition performance of two benzimidazole derivatives, namely:2-(allylthio)-1H-benzo[d]imidazole (SHA) and bis((1H-benzo[d]imidazole-2-yl)thio)methane (BB1C) were studied as a corrosion inhibitors for mild steel (MS) in 1.0 M HCl solution using Weight Loss (WL) measurements, Potentiodynamic Polarization (PDP), Electrochemical Impedance Spectroscopy (EIS), Scanning Electron Microscopy(SEM) and Energy Dispersive X-ray (EDX) analysis. The kinetics of corrosion retardation were inspected by polarization studies, and the respective achievements declared that both compounds could retard corrosion reactions via cathodic/anodic (mixed) inhibition mechanism. The adsorption process on MS surface obeyed Langmuir isotherm. Adsorption and thermodynamic parameters were also evaluated. SEM/EDX analysis strongly supports the obtained results and confirms the existence of a barrier film on the metal surface. Our findings provide deeper insights into understanding the interaction mechanisms of SHA and BB1C with MS surface. Experimental outcomes support the outcomes obtained from DFT and Molecular dynamic (MD) simulation.

Synthesis, characterization, and preliminary in vitro cytotoxic evaluation of a series of 2-substituted benzo [d] [1,3] azoles

A series of benzo [d] [1,3] azoles 2-substituted with benzyl-and allyl-sulfanyl groups were synthesized, and their cytotoxic activities were in vitro evaluated against a panel of six human cancer cell lines. The results showed that compounds BTA-1 and BMZ

One-Pot Synthesis of 2-Benzyl/2-Allyl-Substituted Thiobenzoazoles Using Transition-Metal-Free Conditions in Water

A transition-metal-free protocol for the one-pot synthesis of 2-benzyl/2-allyl-substituted thiobenzoazoles in water was developed. The cyclization of 2-aminothiophenols, 2-aminophenols, and 1,2-phenylenediamines with tetramethylthiuram disulfide (TMTD) gave mercapto benzoheterocycles, and the subsequent C-S coupling with benzyl or allyl halides furnished the desired products in good to excellent yields. This method features transition-metal-free conditions with water as a solvent, an easy performance, mild reaction conditions, a wide substrate scope, and good to excellent yields, thus paving an efficient and useful way to establish a library of potentially active drug molecules.

The activity of magnesium/aluminum 'memory effect' reconstructed hydrotalcites in the microwave-assisted synthesis of 2-benzimidazolethiol and its alkylated derivatives

An efficient and practical methodology for the microwave-assisted synthesis of 2-benzimidazolethiol from 1,2-benzenediamine and carbon disulfide using reconstructed hydrotalcite is described. The corresponding mono- and dialkylated derivatives of 2-benzimidazolethiol were obtained generally in good to excellent yields after short reaction times. Reconstructed hydrotalcite proved to be an efficient and reusable heterogeneous base for the alkylation reactions. Georg Thieme Verlag Stuttgart New York.

An easy and fast ultrasonic selective S-alkylation of hetaryl thiols at room temperature

A series of 2-alkylthio derivatives of hetaryl thiols were synthesized by selective S-alkylation with alkyl halides (bromides and iodides) with ultrasonic irradiation at room temperature. The reaction was found to be generally applicable to hetaryl thiol derivatives with different substituents in the aromatic nucleus and various alkyl halides. The reaction gives high to excellent yields of products with high purity.

Solvent effects and solvation models in the allylation of 2-mercaptobenzimidazole

The second order rate constants of allylation of 2-mercaptobenzimidazole are obtained conductometrically in different protic and aprotic solvents in the temperature range 303-318K. Linear multiple regression analysis results in the LSER log kII = -8.633 + 11.032Y + 6.958P + 0.189α (n = 11, R = 0.931), suggesting that the transition state is more solvated than the reactants due to polarity, polarisability and hydrogen bond donor ability of the solvent.

A new method of synthesis of triazolobenzimidazole

Condensation between dipole 1,3 and 2-alkylthiobenzimidazole was studied. We obtained some compounds derived from triazolobenzimidazole. All the molecules were characterized by 1H NMR, IR, mass and X-rays.

Synthesis and preliminary evaluation of benzimidazole derivatives as antimicrobial agents

A series of 2-alkylsulphanylbenzimidazoles was synthesised and the compounds were evaluated for their in vitro antimicrobial activity. The structures of the compounds were confirmed by 1H-NMR and IR data, and their purity by elemental analysis. Antimycobacterial activities against Mycobacterium tuberculosis and non-tuberculous mycobacteria as well as antifungal activities against Candida albicans, Candida tropicalis, Candida krusei, Candida glabrata, Trichosporon beigelii, Trichophyton mentagrophytes and Aspergillus fumigatus were expressed as the corresponding MIC values. The substances exhibited appreciable antimycobacterial activity, in particular, against non-tuberculous mycobacteria. The activity of the most active compound in the set, 3,5-dinitro derivative 4t, exceeded that of the standard isoniazide against M. kansasii and M. avium. The antifungal activities of the compounds were relatively low. A weak antifungal effect was observed against the dermatophyte Trichophyton mentagrophytes. None of the compounds showed significant inhibitory activity against yeasts.

Synthesis and spectral characterization of 2-mercaptobenzimidazole derivatives using a new active phase transfer reagent under PTC conditions

The phase transfer catalyzed synthesis of 2-Mercaptobenzimidazole derivatives using the new active phase transfer reagent namely, 2- benzilidine-N,N,N,N',N',N'-hexaethyl propane-1,3-diammonium dibromide (Dq-Br) have been described. The structures of all the fifteen compounds have been established by spectroscopic means.