33007-61-3

Usage

Uses

Used in Rubber and Plastic Industry:
2,2'-[thiobis(methylene)]bis-1H-benzimidazole is used as a curing agent for the production of rubber and plastic materials. Its role in crosslinking polymer chains is crucial for improving the mechanical strength, durability, and overall performance of these materials.
Used in Adhesive and Coating Formulation:
In the adhesive and coating industries, 2,2'-[thiobis(methylene)]bis-1H-benzimidazole is utilized as an additive. Its inclusion in formulations helps to enhance the adhesion properties, improve the curing process, and increase the resistance of the final product to various environmental factors.
Used in Antimicrobial Applications:
2,2'-[thiobis(methylene)]bis-1H-benzimidazole is used as an antimicrobial agent in the production of coatings and textiles. Its antimicrobial properties contribute to the development of products that can inhibit the growth of bacteria, fungi, and other microorganisms, thereby improving hygiene and reducing the risk of infections.
Used in Manufacturing Industry:
2,2'-[thiobis(methylene)]bis-1H-benzimidazole is used as a crosslinking agent in the manufacturing industry. Its ability to form covalent bonds between polymer chains is essential for enhancing the physical properties of various materials, such as elasticity, tensile strength, and thermal stability. This makes it a valuable component in the production of a wide range of products, including automotive parts, electronic components, and construction materials.

Upstream product

• 123-93-3 thiodiacetic acid 
• 95-54-5 1,2-diamino-benzene 
• 4857-04-9 2-chloromethyl-1H-benzimidazole 
• 4344-85-8 (1H-benzimidazol-2-yl)methanethiol 

Relevant academic research and scientific papers

Biological activity and molecular structures of bis(benzimidazole) and trithiocyanurate complexes

1-(1H-Benzimidazol-2-yl)-N-(1H-benzimidazol-2-ylmethyl)methanamine (abb) and 2-(1H-benzimidazol-2-ylmethylsulfanylmethyl)-1H-benzimidazole (tbb) have been prepared and characterized by elemental analysis. These bis(benzimidazoles) have been further used in combination with trithiocyanuric acid for the preparation of complexes. The crystal and molecular structures of two of them have been solved. Each nickel atom in the structure of trinuclear complex [Ni3(abb)3(H2O)3(μ-ttc)](ClO4)3?3H2O?EtOH (1), where ttcH3 = trithiocyanuric acid, is coordinated with three N atoms of abb, the N,S donor set of ttc anion and an oxygen of a water molecule. The crystal of [(tbbH2)(ttcH2)2(ttcH3)(H2O)] (2) is composed of a protonated bis(benzimidazole), two ttcH2 anions, ttcH3 and water. The structure is stabilized by a network of hydrogen bonds. These compounds were primarily synthesized for their potential antimicrobial activity and hence their possible use in the treatment of infections caused by bacteria or yeasts (fungi). The antimicrobial and antifungal activity of the prepared compounds have been evaluated on a wide spectrum of bacterial and yeast strains and clinical specimens isolated from patients with infectious wounds and the best antimicrobial properties were observed in strains after the use of ligand abb and complex 1, when at least 80% growth inhibition was achieved.

Structural characterization and antimicrobial activity of 1,3-bis(2-benzimidazyl)-2-thiapropane ligand and its Pd(II) and Zn(II) halide complexes

1,3-Bis(2-benzimidazyl)-2-thiapropane(L) forms 5-coordinate square pyramidal and 4-coordinate tetrahedral, monometallic complexes with PdCl 2 and ZnX2 (X = Cl, Br, I), respectively. In the palladium complex, the ligand acts as a chelating tridentate, through two of the nitrogen atoms in the imidazole ring and the sulfur atom of the bridging group together with two chloride ions forming a rare five coordinate complex. In the zinc halide complexes, the ligand acts as chelating bidentate, via two of the nitrogen atoms combined with two halide ions giving common tetrahedral complexes. The ligand and its complexes are characterized by analytical data and spectroscopic methods such as FT-Raman, FT-IR (mid-IR, far-IR), 1H and 13C NMR. Their antimicrobial activities are evaluated by the minimal inhibitory concentration (MIC) against 10 bacteria, each with multiple, fresh clinical isolates (10-15), and the results are compared with those of ampicillin, ciprofloxacin, cefazolin, ofloxacin, and piperacillin antibacterial agents. The compound's antifungal activities are reported on Candida albicans, Candida utilis, and Cryptococcus neoformans yeasts, each with multiple isolates (10), and the results are referenced with amphotericin-B, fluconazole and flucytosine antifungal agents. In most cases, the compounds show broad-spectrum (Gram+ and Gram-) activities that are either, more active, or equipotent to, the antibiotic and antifungal agents in the comparison tests.

Synthesis and investigation of antimicrobial activity of some bisbenzimidazole-derived chelating agents

The 1,2-bis(2-benzimidazyl)-1,2-ethanediol (1), 1,4-bis(2-benzimidazyl)-1, 2,3,4-butanetetraol (2), 1,3-bis(2-benzimidazyl)-2-thiapropane (3), 1,3-bis(2-benzimidazyl)-2-thia-propane-dihydrochloride (4), 1,5-bis(2- benzimidazyl)-3-thiapentane (5), and 1,5-bis(2-benzimidazyl)-3-thiapentane dihydrochloride (6) chelating ligands are synthesised and characterised by using analytical data and modem spectroscopic methods such as FT-Raman, FT-IR, 1H- and 13C-NMR spectrometers. Their antimicrobial activities are reported by comparing the in vitro activities, with those of ofloxacin, ciprofloxacin, piperacillin, ampicillin and cefazolin antibacterial agents against fresh clinical isolates. Antifungal activities are reported on Candida albicans, Candida utilis, Cryptococcus neoformans fungi, and the results are referenced with amphotericin-B, fluconazole and flucytosine antifungal agents. It has been found that all the compounds have broad spectra activity and was either more active or equipotent to those compared antibiotic and antifungal agents.

Head-to-head bisbenzazole derivatives as antiproliferative agents: design, synthesis, in vitro activity, and SAR analysis

Abstract: In the present work, a series of bisbenzazole derivatives were designed and synthesized as antiproliferative agents. The antiproliferative activity of these compounds was investigated using MTT assay. Bisbenzazole derivatives showed significant antiproliferative activity against all the four tested cancer cell lines. Among the various bisbenzazole derivatives, bisbenzoxazole derivatives exhibited the most promising anticancer activity followed by bisbenzimidazole and bisbenzothiazole derivatives. All the derivatives were found to be less toxic as compared to methotrexate (positive control) in normal human cells, indicating selective and efficient antiproliferative activity of these bisbenzazole derivatives. The structure–activity relationships of heteroaromatic systems and linkers present in bisbenzazole derivatives were analyzed in detail. In silico ADMET prediction revealed that bisbenzazole is a drug-like small molecule with a favorable safety profile. Compound 31 is a potential antiproliferative hit compound that exhibits unique cytotoxic activity distinct from methotrexate. Graphic abstract: Twenty-one bisbenzoxazole derivatives have been designed synthesized and evaluated to be an antiproliferative activity against four human tumor cell lines.[Figure not available: see fulltext.]

Bisbenzimidazole Derivatives as Potential Antimicrobial Agents: Design, Synthesis, Biological Evaluation and Pharmacophore Analysis

In an attempt to design and synthesize a potent class of antimicrobials, 1,2-phenylenediamine derivatives were reacted with various aliphatic and heteroaliphatic dicarboxylic acids to generate a small library of 26 head-to-head bisbenzimidazole compounds (16 – 42) using the polyphosphoric acid method. These compounds were screened for their antibacterial activity and their antifungal activity. Compound 25 showed maximum potency against both Gram-positive and Gram-negative bacterial strains with minimum inhibitory concentration (MIC) values in the range of 7.81 – 31.25 μg/mL. In particular, it showed the maximum MIC values of 7.81 μg/mL against Gram-negative bacteria, which was four-fold more active than the standard drug ampicillin (MIC = 32.25 μg/mL). Compound 19 was found to be the most active against S. aureus with a MIC value of 3.90 μg/mL, whereas the remaining compounds showed only low-to-moderate activity. Furthermore, all compounds exhibited low activity against all fungal strains in comparison to the standard drug fluconazole. I addition, pharmacophore hypotheses were generated to analyze structure–activity relationships between the molecular structures and antimicrobial activities on E. coli. This pharmacophore model can be useful in order to design new antimicrobial drugs. It can be suggested that the substitution of a phenyl ring at the 5/6 and 5′/6′ positions in symmetric bisbenzimidazole derivatives produces compounds with promising antimicrobial activity.

Synthesis, X-ray structure, theoretical investigation, corrosion inhibition and antimicrobial activity of benzimidazole thioether and theirs metal complexes

Synthesis, characterization, corrosion inhibition as well as antimicrobial activity of the coordination compounds {Co(bbms)Cl2}, {Zn(bbms)Cl2}, {Co(btmb)Cl2} and {Zn(btmb)Cl2} containing benzimidazole thioether have been described. Co(bbms) and Zn(bbms) as well as Co(btmb) and Zn(btmb) are isostructural with space group Pbca and P21 respectively. The coordination polyhedron around the metal center for all complexes may be described as a quasi-regular tetragonal geometry. The corrosion inhibition study of these complexes for steel in 0.5?M H2SO4medium has been investigated using potentiodynamic polarization and EIS techniques. These later show the corrosion inhibition ability of the prepared complexes for steel in acid medium. A new procedure has been developed for antimicrobial assay using a solid tablet of the corresponding complexes. These later show moderate to significant antimicrobial activities against: Pseudomonas syringae, Staphylococcus aureus and Pichia caribbica. DFT/BP86 calculations have been carried out on the neutral complexes and on the monoanionic of (1) and (3) forms of singlet and triplet species. The optimized structures reproduce those observed experimentally, while the reduced ones undergo remarkable geometrical parameters variations.

Silphox [POCl3-n(SiO2)n] as a new, efficient, and heterogeneous reagent for the synthesis of benzimidazole derivatives under microwave irradiation

Silphox [POCl3-n(SiO2)n] efficiently catalyzes the condensation of benzene-1,2-diamine with mono and dicarboxylic acids under microwave irradiation to afford benzimidazole derivatives in high yields and short reaction times.

Polymerisation and oligomerisation catalysts

A polymerisation catalyst comprising (1) a transition metal compound of Formula A, and optionally (2) an activating quantity of a Lewis acid activator, Formula (A), wherein Z is a five-membered heterocyclic group containing at least one carbon atom, at least one nitrogen atom and at least one other hetero atom selected from nitrogen, sulphur and oxygen, the remaining atoms in the ring being nitrogen or carbon; M is a metal from Group 3 to 11 of the Periodic Table or a lanthanide metal; E1 and E2 are divalent groups from (i) aliphatic hydrocarbon, (ii) alicyclic hydrocarbon, (iii) aromatic hydrocarbon, (iv) alkyl substituted aromatic hydrocarbon (v) heterocyclic groups and (vi) heterosubstituted derivatives of groups (i) to (v); D′ and D2 are donor groups; X is an anionic group, L is a neutral donor group; n=m=zero or 1; y and z are zero or integers. The catalysts are useful for polymerising or oligomerising 1-olefins.

Synthesis of Some Imidazole- and Pyrazole- Derived Chelating Agents

Procedures involving condensation of o-phenylenediamines with carboxylic acids, and reaction of bifunctional alkyl halides with bifunctional nucleophiles are described.Syntheses are reported of 2,6-bis(2-benzimidazyl)-pyridine, 1,3-bis(2-benzimidazyl)-2-thiapropane, 1,7-bis(2-benzimidazyl)-2,6-dithiaheptane, 2-hydroxymethyl-5,6-dimethylbenzimidazole, 2-chloromethyl-5,6-dimethylbenzimidazole hydrochloride, 1,7-bis(5,6-dimethyl-2-benzimidazyl)-2,6-dithiaheptane, 3,6-bis(1-pyrazolyl)pyridazine, 2-(2-hydroxy-3-methylphenyl)benzimidazole, 2-(2-hydroxyphenyl)benzimidazole, 5-(2-hydroxyphenyl)-3-methyl-1-phenylpyrazole, 3(5)-(2-hydroxyphenyl)-5(3)-methylpyrazole, 3(5)-(2-hydroxyphenyl)-5(3)-phenylpyrazole, and 1,3-bis((5-methylpyridyl)imino)isoindoline.