16109-46-9

Usage

Chemical class

Heterocyclic organic compounds (benzimidazoles)

Molecular structure

Benzimidazole ring with a benzoyl group at the first position and dimethyl groups at the 5th and 6th positions

Potential applications

Pharmaceuticals, agrochemicals

Biological activities

Anti-inflammatory, anti-bacterial, and anti-fungal properties

Synthesis use

Building block for other organic compounds in industrial and research purposes

Precautions

Health and environmental hazards if not properly managed

Upstream product

• 582-60-5 5,6-dimethyl-1H-benzo[d]imida-zole 
• 98-88-4 benzoyl chloride 
• 103-82-2 phenylacetic acid 
• 100-52-7 benzaldehyde 

Downstream Products

• 90108-84-2 (5,6-Bis-dibromomethyl-benzoimidazol-1-yl)-phenyl-methanone 
• 90108-68-2 1-benzoyl-1H-naphth<2,3-d>imidazole-6,7-dicarboxylic anhydride 

Relevant academic research and scientific papers

A azole amide preparation method of the compound

A preparation method of an azole-series amide compound. The invention discloses a method including a reaction that the azole-series amide is synthesized from a carboxylic acid compound and an azole compound with a copper salt as a catalyst and molecular o

Chemoselective acylation of benzimidazoles with phenylacetic acids under different Cu catalysts to give fused five-membered N-heterocycles or tertiary amides

C-N bond formation via a copper-catalyzed aerobic oxidative decarboxylative tandem protocol was realized. The phenylacetic acids which contain ortho-X (X = F or Br) on the aromatic ring will render a fused five-membered heterocycle via a tandem aromatic nucleophilic substitution and aerobic oxidative decarboxylative acylation at the C(sp2)-H bond of benzimidazoles under the Cu(OAc)2/K2CO3/BF3·Et2O catalytic system, while with CuBr as the catalyst and pyridine as the base, N-acylation occurred and tertiary amides were obtained.

Metal-free cross-dehydrogenative coupling of benzimidazoles with aldehydes to N-acylbenzimidazoles

A novel and direct cross-dehydrogenative coupling (CDC) between benzimidazoles with aldehydes promoted by di-tert-butyl peroxide (DTBP) was developed. The reactions generated the corresponding N-acylbenzimidazoles in good yields under metal-free conditions. This method has broad substrate scope and high efficiency.

Defined Dimensional Alterations in Enzyme Substrates. lin-Naphthoadenine and lin-Naphthoadenosine

lin-Naphthoadenine (lin = linear) and lin-naphthoadenosine have been synthesized for the first time, on the basis of the availability of the intermediate lin-naphthohypoxanthine from a shortened, efficient synthesis. 5,6-Dimethylbenzimidazole, protected by a bulky group on N, was subjected to selective benzylic bromination.The tetrabromo product, when treated with sodium iodide under Finkelstein conditions, generated a dibromo-o-xylylene intermediate that could be trapped by maleic anhydride or N-hydroxymaleimide, with aromatization by loss of 2 HBr.This Diels-Alder cycloaddition approach to the otherwise difficult available tetra-β-substituted naphthalenes was followed by stepwise conversions of the terminal anhydride or N-hydroxyimide ring to a suitable substituted pyrimidine ring. lin-Naphthoadenine and lin-naphthoadenosine are brillantly fluorescent, exhibiting high fluorescent yields (Φ = 0.57, 0.64) and long lifetimes (τ = 20.5, 22.4 ns in ethanol purged of oxygen).Neither is a substrate for adenosine deaminase, showing that a lateral extension of 4.8 Angstroem is too great for a satisfactory fit at the enzyme active site, whereas a 2.4-Angstroem extension (lin-benzoadenine and lin-benzoadenosine) is tolerated.