42032-46-2

Usage

Chemical classification

1-octyl-1H-benzo[d]imidazole is a heterocyclic aromatic compound belonging to the imidazoles group.

UV protection

Commonly used as an additive in sunscreen and personal care products to provide protection against harmful UV rays and prevent sunburn.

Light stabilization

Known for its light-stabilizing properties, making it a popular ingredient in plastic and rubber products to prevent degradation caused by UV radiation.

Antifungal potential

Studied for its potential use as an antifungal agent due to its inhibitory effects on fungal growth.

Versatile applications

Used in various industries, including personal care, plastics, agriculture, and more.

Upstream product

• 51-17-2 benzoimidazole 
• 111-83-1 1-bromo-octane 
• 1073-32-1 sodium benzimidazolate 

Relevant academic research and scientific papers

Green synthesis of selenium-N-heterocyclic carbene compounds: Evaluation of antimicrobial and anticancer potential

Three benzimidazolium salts (III-V) and respective selenium adducts (VI-VIII) were designed, synthesized and characterized by various analytical techniques (FT-IR and NMR 1H, 13C). Selected salts and respective selenium N-Heterocycli

Dose-, time-and lipophilicity-dependent silver(I)–N-heterocyclic carbene complexes: Synthesis, characterization and interaction with plasmid and Aedes albopictus DNA

Four new Ag(I)–N-heterocyclic carbene (NHC) complexes (5–8) bearing symmetrically substituted NHC ligands have been synthesized starting from the corresponding benzimidazolium bromide salts which are accessible in a single step from N-substituted benzimid

Synthesis, structure, anticancer, and antioxidant activity of para-xylyl linked bis-benzimidazolium salts and respective dinuclear Ag(I) N-heterocyclic carbene complexes (Part-II)

The article describes synthesis, characterization (NMR, FT-IR, microanalysis, X-ray crystallography), in vitro anticancer, and antioxidant activity of para-xylyl linked bis-benzimidazolium salts and respective dinuclear Ag-NHC complexes. All the compounds were tested for their cytotoxicity against human colorectal cancer cells (HCT 116) and DPPH antioxidant evaluation. According to cell viability measurements using MTT assay, all the tested compounds showed dose-dependent cytotoxic activity against HCT 116 cells. The tested compounds demonstrated significant activity with IC50 values range 0.29-3.30 μM for HCT 116 and % age inhibition 6.37-21.00 for DPPH antioxidant study. 5-Fluorouracil was used as standard drug (IC50 19.2 μM for HCT 116) whereas for DPPH analysis, Gallic acid was used as positive control (% age inhibition 77.68). All the compounds showed potential anticancer activity against human colorectal cancer whereas antioxidant activity was not significant. We found that as the size of N-alkyl substitution on benzimidazolium salt increases its cytotoxicity against cancer decreases whereas a reverse occurs in case of respective complexes.

Synthesis, In silico and in vitro studies of Silver (I)-N heterocyclic carbene complexes

In the present study, four silver based NHC (N-heterocyclic carbene) complexes (1c-4c) were designed and synthesized from their precursor salts (1b-4b). The successful synthesis of salts and complexes was assured through spectroscopic techniques (UV-visible, FTIR, 1H NMR) as well as mass spectrometry. The in silico ADMET study and molecular docking calculations predicted the compounds are good drug candidates having therapeutic potential against multiple cancer targets including COX-1, VEGFA, HIF as well as VGF. Results of in vitro study conducted through MTT assay confirmed that all test compounds have concentration dependent potency but silver complexes (1c-4c) have far superior activity than precursor, salts (1b-4b) and slightly lower than standard drugs (carboplatin and cisplatin) against various cancer cell lines. Among the studied compounds, 3c showed lowest IC50 value of 0.981 ± 0.09, 1.10 ± 0.14 and 0.973 ± 0.12 μg/mL against MCF-7, HCT-116 and A549 respectively. The test compounds were found good antibacterial agents, when screened against bacterial strains (Staphylococcus aureus, Micrococcus luteus, Escherichia coli and S. typhimurium), as well as antioxidant agents when tested against DPPH free radicals.

Benzimidazolium salts prevent and disrupt methicillin-resistant: Staphylococcus aureus biofilms

Emergence of resistant bacteria encourages us to develop new antibiotics and strategies to compensate for the different mechanisms of resistance they acquire. One of the defense mechanisms of resistant bacteria is the formation of biofilms. Herein we show

Carbonylative Acetylation of Heterocycles

Herein, a new procedure for the carbonylative acetylation of heterocycles has been developed. In this process, organic peroxide acts as the methyl source. Various heterocycles were transformed into the corresponding methyl heterocyclic ketones in moderate to good yields.

An efficient strategy for N-alkylation of benzimidazoles/imidazoles in SDS-aqueous basic medium and N-alkylation induced ring opening of benzimidazoles

A sustainable route for the N-1 alkylation of imidazole and benzimidazole derivatives has been developed under volatile organic solvent free condition in alkaline water-SDS system. Incorporation of SDS in the reaction medium enhances the reaction rate by suppressing the solubility issue that arises for different substrates. This method provides high yield of the alkylated product in a shorter reaction time. For reactive alkyl halides reaction proceeds at ambient temperature whereas in the cases of less reactive alkyl halides require 55–60 °C to complete alkylation process. N-alkylation induced ring opening of the heterocyclic ring in benzimidazole derivatives to multifunctional aromatic compounds were noticed at 60 °C when more than two equivalents of alkyl halide was used.

Activation of Michael Acceptors by Halogen-Bond Donors

Extending earlier studies on iodine catalysis, experimental investigations show that various halogen-bond donors can also be employed to accelerate the Michael addition between trans -crotonophenone and indole. Solvent as well as counteranion effects have been analyzed, and kinetic and computational investigations provide additional insights into the mode of activation.

Effect of lipophilicity of wingtip groups on the anticancer potential of mono N-heterocyclic carbene silver(I) complexes: Synthesis, crystal structures and in vitro anticancer study

A series of symmetrically n-alkyl-substituted mono benzimidazolium salts with steady increase in n-alkyl chain length have been prepared by stepwise N-alkylation resulting in salts (1–8). The mono N-heterocyclic carbene (NHC)–Ag(I) complexes (9–16) derived from the respective salts were readily accessible by in situ deprotonation using Ag2O. All the salts and the complexes were characterized using Fourier transform infrared, 1H NMR, 13C NMR and elemental analyses. Furthermore, the structures of salts 3 and 7 and complex 16 were elucidated using X-ray crystallography, which established that this mono NHC–Ag(I) complex has a linear bis-carbene arrangement (C2–Ag). The proligands and the respective Ag(I) complexes were studied for their in vitro anticancer potential against human colon cancer cell line (HCT-116) using 5-fluorouracil as a standard. From the IC50 values of all the tested compounds, it can be postulated that there is an influential relationship between the increase in chain length of the wingtip n-alkyl groups and the anticancer potential. The proligands 4–8 and their respective complexes 12–16 with long n-alkyl chain lengths (n?=?6–10) showed better IC50 values (0.3–3.9 μM) than the standard drug with the complexes displaying markedly better antiproliferation activity against HCT-116 cell line than the respective proligands and the standard drug (IC50?=?10.2 μM).

Synthesis, crystal structure, in vitro anticancer and in vivo acute oral toxicity studies of tetramethylene linked bis-benzimidazolium salts and their respective dinuclear Ag(I)–NHC complexes

The proligands of the series tetramethylenebis(N-n-alkylbenzimidazolium bromide) (where n?=?3–10) (1–8) as N-heterocyclic carbene (NHC) precursors have been prepared by reacting the initially synthesized N-n-alkyl benzimidazole with 1,4-dibromobutane in 2?:?1 M ratio. A reaction of Ag2O with 1–8 resulted in the formation of Ag(I) complexes tetramethylenebis{(N-n-alkylylbenzimidazol-2-ylidene)silver(I)hexafluorophosphate} (9–16), respectively. All the synthesized compounds were characterized by FT-IR, 1H NMR, 13C NMR, atomic absorption and elemental analysis. Single-crystal X-ray diffraction study on tetramethylenebis{(N-n-octylbenzimidazol-2-ylidene)silver(I)hexafluorophosphate} (14) has revealed that the complex exists as a dinuclear compound. All compounds were assessed for their antiproliferation test on human colorectal cancer cell line (HCT 116). Interestingly, increasing the n-alkyl chain length from n?=?3 to 10 of the proligands and their respective complexes showed trends in increased cytotoxicity against human colon cancer cell line. Cytotoxicity data showed that tetramethylene linked bis-benzimidazolium salts and their respective dinuclear Ag(I)–NHC complexes can be useful therapeutic agents against colon cancer.