6965-02-2

Basic information

• Product Name: 2-(1H-benziMidazol-2-yl)-1H-benziMidazole
• Synonyms: 2-(1H-benziMidazol-2-yl)-1H-benziMidazole;1H,1'H-2,2'-bibenzo[d]imidazole
• CAS NO: 6965-02-2
• Molecular Formula: C₁₄H₁₀N₄
• Molecular Weight: 234.256
• EINECS: -0
• Mol File: 6965-02-2.mol

Chemical Properties

• Melting Point: >200 °C (decomp)
• Boiling Point: 542.8°Cat760mmHg
• Flash Point: 263.3°C
• Appearance: /
• Density: 1.41g/cm³
• Storage Temp.: 2-8°C
• PKA: 10.65±0.10(Predicted)
• CAS DataBase Reference: 2-(1H-benziMidazol-2-yl)-1H-benziMidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(1H-benziMidazol-2-yl)-1H-benziMidazole(6965-02-2)
• EPA Substance Registry System: 2-(1H-benziMidazol-2-yl)-1H-benziMidazole(6965-02-2)

Safety Data

• Hazardous Substances Data: 6965-02-2(Hazardous Substances Data)

Usage

Uses

Used in Antifungal Applications:
2-(1H-Benzimidazol-2-yl)-1H-benzimidazole is used as an antifungal agent for treating various fungal infections. It is effective against conditions such as athlete's foot, jock itch, and ringworm due to its ability to disrupt fungal cell membranes.
Used in Topical Formulations:
In the pharmaceutical industry, 2-(1H-Benzimidazol-2-yl)-1H-benzimidazole is used as an active ingredient in topical formulations like creams and sprays. These formulations facilitate the direct application to the affected areas, providing targeted treatment for fungal infections.
Used in Treating Pityriasis:
2-(1H-Benzimidazol-2-yl)-1H-benzimidazole is also used as a medicinal treatment for pityriasis, a skin condition characterized by the lightening or darkening of the skin. Its antifungal properties help address the underlying fungal infection contributing to the condition.

Upstream product

• 694-59-7 pyridine N-oxide 
• 51-17-2 benzoimidazole 
• 67-56-1 methanol 
• 3878-19-1 fuberidazole 
• 95-54-5 1,2-diamino-benzene 
• 2533-69-9 methyl 2,2,2-trichloroacetimidate 
• 2849-93-6 2-benzimidazolecarboxylic acid 
• 2213-63-0 2,3-dichloroquinoxaline 
• 15804-19-0 quinoxaline-2,3-dione 
• 471-46-5 Oxalamide 
• 56-81-5 glycerol 
• 144-62-7 oxalic acid 

Downstream Products

• 675108-81-3 C₂₅H₁₇N₅O 
• 675108-80-2 C₂₅H₁₇N₅O₂ 
• 114074-83-8 {Cu(bibenzimidazolate)(triphenylphosphine)} 
• 114074-90-7 {Cu(bibenzimidazole)(triphenylphosphine)2}BF₄ 
• 92922-66-2 [Au(C₆F₅)2]2((C₆H₄(N)2C)2) 
• 107544-37-6 [Mn(CO)2(P(OC₆H₅)3)2((C₇N₂H₅)(C₇N₂H₄))] 
• 79747-46-9 {(1,1-bis(diphenylphosphino)methane)Au2}(μ-2,2'-bibenzimidazolato) 
• 84076-81-3 {(1,2-bis(diphenylphosphino)ethane)Au2}(μ-2,2'-bibenzimidazolato) 
• 79188-26-4 (C₆H₅)4C₄Au(C₁₄H₈N₄)Au(C₆H₅)4C₄ 
• 160987-30-4 [(η(6)-p-cymene)Ru(PPh3)(C14H9N4)]BF4 
• 207388-79-2 [Cu(C₆H₄N₂(H)C)2(P(C₆H₅)3)2]⁽¹⁺⁾*Cl^(1-)=[Cu(C₆H₄N₂(H)C)2(P(C₆H₅)3)2]Cl 
• 202006-35-7 [Ag(P(C₆H₅)3)2(C₆H₄N₂CH)2]⁽¹⁺⁾*CH₃COO^(1-)=[Ag(P(C₆H₅)3)2(C₆H₄N₂CH)2]CH₃COO 
• 207388-80-5 [Cu(C₆H₄N₂(H)C)2(P(C₆H₅)3)2]⁽¹⁺⁾*CH₃COO^(1-)=[Cu(C₆H₄N₂(H)C)2(P(C₆H₅)3)2](CH₃COO) 
• 202006-36-8 [Ag(P(C₆H₅)3)2(C₆H₄N₂CH)2]⁽¹⁺⁾*CF₃COO^(1-)=[Ag(P(C₆H₅)3)2(C₆H₄N₂CH)2]CF₃COO 

Relevant articles and documents

The use of diethylene glycol in the synthesis of 2,2'-bibenzimidazole from o-phenylenediamine and oxalic acid

One- and two-step syntheses of 2,2'-bibenzimidazole were compared. Diethylene glycol was used as solvent that provides good solubility of the substrates. The limitation of the one-step preparation is the formation of the by-product, fluoflavine. The two-step synthesis proceeds with the separation of the intermediate product, 1,4-dihydroquinoxaline-2,3-dione, and the final product is only 2,2'-bibenzimidazole. The total yield of the two-step synthesis is above 85%.

Gold catalysis opens up a new route for the synthesis of benzimidazoylquinoxaline derivatives from biomass-derived products (glycerol)

Process intensification by using well-defined solid catalysts able to perform one-pot multistep reactions is one of the open fronts in heterogeneous catalysis. This is even more relevant if new, more efficient synthesis routes are open. Herein, a gold catalyst was used to synthesize benzimidazoylquinoxalines compounds by two efficient and selective novel methods in a multistep one-pot methodology. The first method involved the synthesis of benzimidazoylquinoxaline compounds with the same substituents in both heterocycles through oxidation-cyclization of glycerol with o-phenylenediamine derivatives, whereas the second one allowed the synthesis of benzimidazoylquinoxalines compounds with different substituents in each aromatic ring through coupling of o-phenylenediamine derivatives with glyceraldehyde in a first stage to produce the benzimidazol compound as an intermediate, followed by an oxidation-cyclization with another o-phenylenediamine compound in a second stage. Both stages were performed by using gold nanoparticles supported on nanoparticulated ceria (Au/CeO2) as the catalyst and air as the oxidant, in absence of any homogeneous reagent. A reaction mechanism has been proposed. A smooth route: Benzimidazoylquinoxaline derivatives can be obtained in good yields through one-pot oxidative coupling of glycerol or glyceraldehydes with 1,2-phenylenediamines in a two-step reaction, using Au/CeO2 as the catalyst, base-free conditions, mild temperature, and air as the oxidant. Copyright

Efficient synthesis and characterization of novel bibenzimidazole oligomers and polymers as potential conjugated chelating ligands

A simple and mild condensation route for the synthesis of novel bibenzimidazole oligomers and polymers is reported here using methyl 2,2,2-trichloroacetimidate as a key starting material. The dimer, trimer, tetramer, and polymers of bibenzimidazole were synthesized as a new series of potential conjugated chelating ligands for metallopolymer studies. The polymers show a maximum absorption at around 400 nm. The optical band gap of the polymer was estimated to be 2.68 eV.

Quantitative cascade condensations between o-phenylenediamines and 1,2-dicarbonyl compounds without production of wastes

o-Phenylenediamines 1 underwent a series of cascade condensations with 1,2-dicarbonyl compounds to afford quantitative yields (eight cases) of heterocycles in solid-state syntheses that avoided waste formation. The products were produced in pure form and did not require purifying workup. The components were ball-milled in stoichiometric ratio, or in exceptional cases they were melted together and heated in the absence of solvents (some of them giving quantitative yields). Benzils and 2-hydroxy-1,4-naphthoquinone afforded quinoxaline derivatives 3 and 5, 2-oxoglutaric acid gave a 3-oxodihydroquinoxaline 7, and oxalic acid afforded the dihydroquinoxaline-2,3-dione 9. This last condensed with la in the melt, to afford a mixture of bis(benzimidazolyl) 10 and fluoflavin 11. Alloxane hydrate provided a 100% yield of the 3-oxodihydroquinoxaline-2-carbonylureas 15/16 at room temperature. Parabanic acid required a melt reaction providing a 78% yield of 3-oxodihydroquinoxalinyl-2-urea 22 and side products. Despite numerous reaction steps, most of these uncatalyzed stoichiometric reactions proceeded quantitatively in the solid state to give only one product (plus water), with unsurpassed atom economy. If catalysis with HCl was tried, the results were inferior. If melt reactions were required it appeared to be advantageous to have the products crystallize directly at the reaction temperature. The synthetic results have been interpreted mechanistically and compared to some similar solution reactions that do not exhibit the benefits of the solid-state techniques. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).

Studies on synthesis of 2-acetylbenzimidazole and related benzimidazole derivatives

Condensation of o-phenylenediamine (1) with propanoic acid under Phillips' conditions gives 2-ethylbenzimidazole (2). Attempts to oxidise 2 to 2-acetylbenzimidazole (3) using H2O2, SeO2, KMnO4/acetone were unsuccessful. Condensation of 2 with benzaldehyde yields 2-(α-methylstyryl)benzimidazole (4) which on oxidation with KMnO4 gives benzimidazole-2-carboxylic acid (5) as the sole product. Reaction of 1 with pyruvic acid results in 3-methylbenzo-1H-dihydropyrazine-2-one (7) rather than 3 as the major product. Treatment of 1 with formic acid gives the known compound benzimidazole (9) which with acetic anhydride in the presence of NaOAc does not yield 3. Reaction of 1 with lactic acid under Phillips' conditions gives 2-(α-hydroxyethyl)benzimidazole (10) which on oxidation with acid dichromate, however, yields 3. Studies on syntheses and spectral properties of related benzimidazoles are reported.

Photochemistry of 2-(2-Furyl)-benzimidazole (Fuberidazole)

The photodegradation of 2-(2-furyl)-benzimidazole (Fuberidazole 1) has been reinvestigated employing advanced HPLC-UV/VIS techniques and fluorescence emission and excitation spectroscopy in methanol at natural pH, in acidic medium and in aqueous solutions at pH 7 and 3, and four main products benzimidazole-2-carboxyclic acid 3, its methyl ester 2, 1-methoxy benzimidazole 5, methyl 4-oxo-2-benzimidazole crotonate 7 (cis and trans isomers) besides benzimidazole 4 and 2,2'-bibenzimidazole 6 and other side products have been isolated and characterized.The kinetics of the photodegradation process was followed independently be HPLC-UV and fluorescence emission showing a significant similarity of the curve habit; this allows to monitor a photodegradation at very low concentrations (5*10-5 - 5*10-6 M).The quantum yield of disappearance of Fuberidazole has been determined. Key Words: 2-(2-Furyl)-benzimidazole, Fuberidazole, Photodegradation, HPLC Separation, Fluorescence Emission

Dimerizations of ?-Rich N-Heteroaromatic Compounds and Xantin Derivatives

Dimerization reactions of six ?-rich N-heteroaromatic compounds (2-7) and five xantin derivatives (8-12) in the presence of platinated palladium-carbon (Pd-Py/C) catalyst were investigated.N-Methylimidazole (2), benzimidazole (4) and N-methylbenzimidazole (5) condensed dehydrogenatively to afford the corresponding symmetric dimers when heated in the presence of Pd-Pt/C catalyst and pyridine oxide (1).On the other hand, imidazole (3), pyrazole (6) and N-methylpyrazole (7) did not dimerize under the same conditions.The same reactions using caffeine (10), 1,7-dimethylhypoxanthine (9) gave the corresponding dimers.

Environmental Effects on the Absorption and Fluorescence Spectral Characteristics of Benzimidazole-2-carboxylic Acid and Its Esters

The absorption and fluorescence spectra of benzimidazole-2-carboxylic acid (BIA) and 5-chlorobenzimidazole-2-carboxylic acid (CBIA) have clearly indicated that benzimidazole (BI) ring and -COOH group are coplanar to each other and are held together in a rigid frame by intramolecular hydrogen-bonding.Dual fluorescence is observed in polar and hydrogen bonding solvents.The short wavelength fluorescence band is assigned to a structure where the -COOH group is perpendicular to the BI moiety and the long wavelength fluorescence band to the planar configuration.This is further manifested from the spectral characteristics of the ester of 5-chlorobenzimidazole-2-carboxylic acid (CBIM).Various prototropic reactions taking place in S0 ans S1 states for all the three molecules are studied in the H0/pH/H- range of -10 to 16.All the dissociation constants are determined, both in the S0 and S1 states and are discussed.