3705-86-0

Usage

Uses

Used in Pharmaceutical Industry:
1,3-dihydro-5,6-dinitro-2H-benzimidazol-2-one is used as a key compound for the preparation of a naked-eye on-off-on polypyridyl-based ruthenium complex light switch. This application is based on a reversible conformational switch of G-quadruplex DNA, which can be significant in the development of new drugs and therapies.
Used in Environmental Science:
In the field of environmental science, 1,3-dihydro-5,6-dinitro-2H-benzimidazol-2-one is used for studying the reduction of nitroaromatic compounds by NAD(P)H:quinone oxidoreductase (NQO1). This research helps in understanding the role of electron-accepting potency and structural parameters in substrate specificity, which is crucial for the development of methods to remediate contaminated environments and improve waste management strategies.
Used in Chemical Research:
1,3-dihydro-5,6-dinitro-2H-benzimidazol-2-one serves as an important intermediate in the synthesis of various chemical compounds, particularly those with potential applications in the pharmaceutical, agrochemical, and materials science industries. Its unique chemical properties make it a valuable building block for the development of new molecules with specific functions and properties.

InChI:InChI=1/C7H4N4O5/c12-7-8-3-1-5(10(13)14)6(11(15)16)2-4(3)9-7/h1-2H,(H2,8,9,12)

Upstream product

• 615-16-7 1,3-dihydro-2H-benzimidazol-2-one 
• 95-54-5 1,2-diamino-benzene 
• 93-84-5 5-nitro-2,3-dihydro-1H-benzimidazol-2-one 

Downstream Products

• 1849-05-4 5,6-dinitro-2-chlorobenzimidazole 

Relevant academic research and scientific papers

Synthesis of a Water-Soluble Derivative of Cyclohexatriacontane-1,2,13,14,25,26-hexone

Cyclotrimerization of cyclododecyne and cyclopentadecyne to the corresponding benzene derivatives is catalyzed by Co2(CO)8 and by TiCl3.Ozonolysis of these aromatic compounds, followed by reductive workup and treatment with derivatives of o-phenylenediamine gives in ca. 3percent yield macrocyclic ring compounds: cyclohexatriacontatrisquinoxaline (9), cyclohexatriacontatris(1H,3H-2-oxaimidazoquinoxaline-1,3-di-α-acetate) (17), and cyclopentatetracontatrisquinoxaline (10).These compounds do not s hown shape selectivity in facilitated transport of representative hydrocarbons in water.

Synthesis and characteristic of 5,6-dinitro and 5,6-diaminobenzimidazolone- 2

(Chemical Equation Presented) 5,6-Dinitro and 5,6-diaminobenzimidazolone-2 can be synthesized at a sufficiently high purity and yield to permit its large scale production in an economically feasible manner. The results of our studies derived optimum conditions for the nitration process necessary to obtain pure 5,6-dinitriobenzimidazolone-2.

2+: A colorimetric molecular "light switch" and powerful stabilizer for G-quadruplex DNA

A new ruthenium complex, [Ru(bpy)2dppz-idzo]2+ (bpy = 2,2′-bipyridine, dppz-idzo = dipyrido-[3,2-a:2′,3′-c] phenazine-imidazolone), was synthesized and characterized. The luminescent titrations showed that the Ru-complex exhibited an outstanding "light switch" effect with an emission enhancement factor of about 300 in the presence of G-quadruplex DNA in a K+ solution. This remarkable "light switch" behavior can even be observed by the naked eye under irradiation with UV light. To get an insight into the "light switch" mechanism, quantum-chemical calculations were performed based on the DFT/TDDFT/PCM method at the B3LYP/6-31G* level. Furthermore, the CD titrations and thermal melting experiments indicated that [Ru(bpy) 2dppz-idzo]2+ could not only induce the formation of an antiparallel G-quadruplex structure in the absence of monocations, but also has the ability to stabilize the G-quadruplex architecture, implying potential applications in anticancer therapeutics. Both the "light switch" effect and the structure stabilization ability of [Ru(bpy)2dppz-idzo] 2+ were found to be superior to the well-known DNA molecular "light switch" [Ru(bpy)2dppz]2+. Finally, a "sandwich-like" binding model was proposed on the basis of molecular docking simulations.

Nitro derivatives of 1,3-dihydrobenzimidazol-2-one: II. Rearrangement of N-nitrobenzimidazol-2-ones

N-Nitrobenzimidazol-2-ones readily undergo rearrangement to C-nitro derivatives on heating in various solvents (ethyl acetate, butyl acetate, acetonitrile, acetone, dioxane, o-dichlorobenzene, anisole, acetic acid). This rearrangement was used to develop

Nitro Derivatives of 1,3-Dihydrobenzimidazol-2-one: I. synthesis of N-Nitrobenzimidazol-2-ones

1,3,5,6-Tetranitro-2,3-dihydro-1H-benzimidazol-2-one, 1,5,6-trinitro-2,3- dihydro-1H-benzimidazol- 2-one, and 1,4,5,6-tetranitro-2,3-dihydro-1H- benzimidazol-2-one were synthesized for the first time by nitration of 5,6-di- and 4,5,6-trinitro-2,3-dihydro-

Preparation method for 5,6-diaminobenzimidazolone-2

The invention belongs to the field of chemical synthesis and particularly relates to a preparation method for 5,6-diaminobenzimidazolone-2. The preparation method is characterized in that in a nitration reaction, dichloroethane serves as a solvent, and phosphorus pentoxide serves as a catalyst, so that the defect in the traditional process that a large volume of waste acid is generated due to the fact that concentrated sulfuric acid serves as the solvent can be avoided; and in a reducing reaction, water serves as a solvent and can be recycled, so that the requirements on green chemistry are met. According to the preparation method disclosed by the invention, the process is stable, the operation is simple, and the emission of waste gases, waste water and waste residues is reduced, so that the preparation method is applicable to large-scale industrial production.

LIGAND, METAL COMPLEX COMPOUND CONTAINING THE SAME, AND METHOD FOR PRODUCING THE SAME, AND METHOD FOR PRODUCING MOLECULAR DEVICE

A ligand contains: a benzimidazole skeleton; and functional groups at the 5-position and the 6-position of the benzimidazole skeleton. The functional group is capable of forming a coordinate bond with a metal, and contains a nitrogen atom.