2620-85-1

Usage

Uses

Used in Green Activation Techniques:
2-(3,4-DIMETHOXYPHENYL)-1H-BENZIMIDAZOLE is used as a green activator in chemical reactions, promoting environmentally friendly processes that minimize the use of hazardous substances and reduce waste generation.
Used in Antifungal Applications:
In the field of agriculture and food preservation, 2-(3,4-DIMETHOXYPHENYL)-1H-BENZIMIDAZOLE is used as an antifungal agent to inhibit the growth of fungi and prevent spoilage, thereby extending the shelf life of food products and protecting crops from fungal diseases.
Used in Antimicrobial Applications:
2-(3,4-DIMETHOXYPHENYL)-1H-BENZIMIDAZOLE also exhibits antimicrobial properties, making it suitable for use in various industries such as healthcare, pharmaceuticals, and cosmetics. It can be employed to inhibit the growth of bacteria and other microorganisms, ensuring the safety and efficacy of products and reducing the risk of infections.

InChI:InChI=1/C15H14N2O2/c1-18-13-8-7-10(9-14(13)19-2)15-16-11-5-3-4-6-12(11)17-15/h3-9H,1-2H3,(H,16,17)

Upstream product

• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 95-54-5 1,2-diamino-benzene 
• 88-74-4 2-nitro-aniline 
• 94687-10-2 ethyl-3-(3,4-dimethoxyphenyl)-3-hydroxy-2-(2-methoxyphenoxy)propanoate 
• 1835-02-5 2-Bromo-1-(3,4-dimethoxyphenyl)ethanone 
• 29389-04-6 2-(2,6-dimethoxyphenoxy)-1-(3,4-dimethoxyphenyl)ethan-1-one 
• 22675-96-3 2-methoxyphenoxy-3',4'-dimethoxyacetophenone 
• 140455-40-9 1-(3,4-dimethoxyphenyl)-2-phenoxy-1-ethanone 
• 10535-17-8 1-(3,4-dimethoxyphenyl)-2-(methoxyphenoxy)propane-1,3-diol 
• 10548-77-3 1-(3,4-dimethoxyphenyl)-3-hydroxy-2-(2-methoxyphenoxy)propan-1-one 
• 1131-62-0 1-(3,4-dimethoxyphenyl)ethanone 
• 4732-70-1 3,4-dimethoxyphenylglyoxylic acid 
• 5763-61-1 3,4-dimethoxybenzylamine 
• 68413-92-3 sodium (3,4-dimethoxyphenyl)(hydroxy)methanesulfonate 

Downstream Products

• 329082-06-6 2-(4,5-dimethoxy-2-nitrophenyl)-1H-benzo[d]imidazole 
• 1313402-01-5 2-(3',4'-dimethoxyphenyl)-1-methylsulphanylmethyl-1H-benzimidazole 
• 403707-03-9 1-ferrocenylmethyl-2-(3,4-dimethoxyphenyl)-1H-benzimidazole 

Relevant academic research and scientific papers

One-Pot Transformation of Lignin and Lignin Model Compounds into Benzimidazoles

It is a challenging task to simultaneously achieve selective depolymerization and valorization of lignin due to their complex structure and relatively stable bonds. We herein report an efficient depolymerization strategy that employs 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as oxidant/catalyst to selectively convert different oxidized lignin models to a wide variety of 2-phenylbenzimidazole-based compounds in up to 94 % yields, by reacting with o-phenylenediamines with varied substituents. This method could take full advantage of both Cβ and/or Cγ atom in lignin structure to furnish the desirable products instead of forming byproducts, thus exhibiting high atom economy. Furthermore, this strategy can effectively transform both the oxidized hardwood (birch) and softwood (pine) lignin into the corresponding degradation products in up to 45 wt% and 30 wt%, respectively. Through a “one-pot” process, we have successfully realized the oxidation/depolymerization/valorization of natural birch lignin at the same time and produced the benzimidazole derivatives in up to 67 wt% total yields.

Oxidative coupling of primary amines to imines catalyzed by CoCl2·6H2O

A high-performance, readily available and eco-friendly cobalt catalyst has been suggested for the first time for the additive-free oxidative coupling of primary amines to imines. Different substituted benzylamine and heteroaryl methanamine compounds could be transformed into their corresponding imines in good to excellent yields over this catalyst. Meanwhile, it has been demonstrated that this catalyst can also afford the oxidative coupling of various benzylamines with o-phenylenediamine to produce benzimidazole derivatives in medium to good yields.

Diversity in Heterocycle Synthesis Using α-Iminocarboxylic Acids: Decarboxylation Dichotomy

Despite the structural similarity with imines, α-iminocarboxylic acids have seldom been used in heterocycles synthesis. The reactions of ortho-substituted anilines and arylglyoxylic acids in DMSO at 40 °C gave various benzo-fused five- to six-membered N-heterocycles in good to excellent yields. The reaction proceeds via intramolecular Michael addition of α-iminocarboxylic acids, generated in situ, with an ortho-substituted nucleophile, yielding an isolable unprecedented tetrahedral carboxylic acids, which upon decarboxylation without any aid of additional reagents forms the N-heterocycles. DMSO is crucial in this reaction, perhaps because of improved solubility and the ease of decarboxylation of these tetrahedral carboxylic acids. However, a copper-catalyzed reaction of ortho-substituted anilines and 2-bromoarylglyoxylic acids gave a dibenzo-fused seven-membered N-heterocycle under a basic reaction condition. Unlike intramolecular cyclization with α-iminocarboxylic acids in the first case, α-iminocarboxylic acid undergoes a competitive decarboxylation under the copper-catalyzed conditions, which upon subsequent heteroarylation form the heterocycles. Taken together, the study described herein represents two different modes of decarboxylation observed with α-iminocarboxylic acids, leading to the synthesis of divergent heterocycles and pharmaceuticals, which remained unexplored previously.

A heterogeneous catalytic strategy for facile production of benzimidazoles and quinoxalines from primary amines using the Al-MCM-41 catalyst

This study reports a straightforward heterogeneous catalytic (Al-MCM-41) approach to synthesize nitrogen heterocycle moieties from primary amines under solvent-free conditions. The Al-MCM-41 catalyst was prepared using a hydrothermal method and characterized by various analytical techniques. The probability and limitations of the catalytic methodology were presented with various substrates. The catalytic method grants an attractive route to a wide variety of benzimidazole and quinoxaline moieties with good to excellent yields. The gram scale reaction and reusability (up to five cycles) of the Al-MCM-41 catalyst would greatly benefit industrial applications. This journal is

Synthesis of novel benzimidazoles at room temperature, under solvent-free condition and their biological studies

Abstract: An efficient and facile synthesis of substituted novel benzimidazoles (3a–3h) mediated by fruit juices viz. Cocos nucifera L. juice, Citrus limetta juice and Citrus sinensis L. juice, via condensation of substituted aldehydes (1a–1h) and o-pheny

Synthesis, molecular docking, in silico ADME, and EGFR kinase inhibitor activity studies of some new benzimidazole derivatives bearing thiosemicarbazide, triazole, and thiadiazole

Epidermal growth factor receptor (EGFR), one of the important targets in the development of the anticancer compound, is a member of the ErbB receptor tyrosine kinase receptor family and is highly expressed in solid tumors. Inhibition of EGFR is important

Development of homogeneous polyamine organocatalyst for the synthesis of 2-aryl-substituted benzimidazole and benzoxazole derivatives

A new polyamine was prepared by the ring opening polymerization of epichlorohydrin and properly characterized. The catalytic property of the prepared polymer was assessed by synthesizing 2-aryl-substituted benzimidazole and benzoxazole derivatives by the conjugation of o-phenylenediamine/o-aminophenol with various aromatic aldehydes in the presence of atmospheric oxygen. Significant attributes of the present synthesis include short reaction time, good to excellent yield, high purity, easy reusability, and room temperature reaction. The reaction was carried out in the absence of any metal catalyst and other cooxidants.

Reevaluating the synthesis of 2,5-disubstituted-1H-benzimidazole derivatives by different green activation techniques and their biological activity as antifungal and antimicrobial inhibitor

A comparative study concerned with the preparation of diversely substituted-1H-benzimidazole under different green activation techniques and conventional methods is reported. Data are collected for infrared, ultrasound, microwave, and simultaneous irradiation with US and IR sources, as this last strategy shows an important improvement. Further, the small library of potentially bioactive benzimidazole 17-76 synthesized was screened as an antifungal and antimicrobial agent. Strong activity against Candida albicans and Staphylococcus aureus was observed. Remarkably, 2-(4-aminophenyl)-5-phenylamino-1H-benzimidazole 63 resulted better than that of reference drugs miconazole with a zone of inhibition up to 42 mm. Likewise, 2-(2-aminophenyl)-1H-benzimidazole 21 showed substantial antimicrobial activity against MRSA strain. When assayed by the microdilution method, this azaheterocyclic compound presented a minimum inhibitory concentration (MIC) ≥ 16.4 μg/100 mL and a bacterial percentage reduction of 96%.

Metal-organic framework mediated expeditious synthesis of benzimidazole and benzothiazole derivatives through an oxidative cyclization pathway

Herein, we report the facile synthesis of various benzimidazoles and benzothiazoles by using the NH2-MIL-125(Ti) MOF as an efficient oxidant-free heterogeneous catalyst with good yield. Adsorption of the substrate on the NH2-MIL-125(Ti) MOF surface through electron deficient Ti4+ sites initiates the reaction. The broad substrate scope and high reusability of this catalyst are attractive for synthesis of a wide range of medicinally active benzimidazole and benzothiazole derivatives.

Synthesis & anticancer evaluation of new substituted 2-(3,4- Dimethoxyphenyl)benzazoles

Background: The benzazole nucleus is found in many promising small molecules such as anticancer and antibacterial agents. Bendamustine (Alkylating agent), Nocodazole (Mitotic inhibitor), Veliparib (PARP inhibitor), and Glasdegib (SMO inhibitor) are being clinically used as anticancer therapeutic which bear benzimidazole moiety. Based on the principle of bioisosterism, in the present work, 23 compounds belonging to 2-(3,4-dimethoxyphenyl)benzazoles and imidazopyridine series were synthesized and evaluated for their anticancer and antimicrobial activities. Objective: A series of new 2-(3,4-dimethoxyphenyl)-1H-benz(or pyrido)azoles were synthesized and evaluated for their anticancer and antimicrobial activities. Method: N-(5-chloro-2-hdroxyphenyl)-3,4-dimethoxybenzamide 1, was obtained by the amidation of 2-hydroxy-5-chloroaniline with 3,4-dimethoxybenzoic acid by using 1,1'-carbonyldiimidazole. Cyclization of 1 to benzoxazole derivative 2, was achieved by p-toluenesulfonic acid. Other 1H-benz(or pyrido)azoles were prepared by the reaction between 2-aminothiophenol, ophenylenediamine, o-pyridinediamine with sodium metabisulfite adduct of 3,4-dimethoxybenzaldehyde. The NMR assignments of the dimethoxy groups were established by the NOESY spectra. Results: Compound 12, bearing two chlorine atoms at the 5(4) and 7(6) positions of the benzene moiety of benzimidazole was found the most potent analogue against A549 cells with the GI50 value of 1.5 μg/mL. Moreover, 24 showed remarkable cell growth inhibition against MCF-7 and HeLa cells with the GI50 values of 7 and 5.5 μg/mL, respectively. The synthesized compounds have no important antibacterial and antifungal activities. Conclusion: It could be concluded that the introduction of di-chloro atoms at the phenyl ring of 2-(3,4-dimethoxyphenyl)-1H-benzimidazoles increases significant cytotoxicity to selected human tumor cell lines in comparison to other all benzazoles synthesized. Unsubstituted 2-(3,4- dimethoxyphenyl)-imidazopyridines also gave good inhibitory profile against A549 and HeLa cells.