78581-99-4

Usage

Uses

Used in Pharmaceutical Industry:
1H-Benzimidazole,5,6-difluoro-(9CI) is used as a potential pharmacological agent for its anti-cancer, anti-inflammatory, anti-viral, and anti-microbial properties. The presence of fluorine atoms may enhance its activity and selectivity in various therapeutic applications.
Used in Agrochemical Industry:
1H-Benzimidazole,5,6-difluoro-(9CI) is used as a potential active ingredient in agrochemicals, leveraging its anti-microbial and anti-viral properties to protect crops and enhance agricultural productivity.
Used in Material Science:
1H-Benzimidazole,5,6-difluoro-(9CI) is used in the development of new materials, taking advantage of its unique chemical and physical properties to create innovative products for various industrial applications.
Note: The specific applications and industries mentioned are inferred based on the general properties of benzimidazole compounds and the presence of fluorine atoms. Further research and investigation are necessary to confirm the exact uses and benefits of 1H-Benzimidazole,5,6-difluoro-(9CI) in these areas.

InChI:InChI=1/C7H4F2N2/c8-4-1-6-7(2-5(4)9)11-3-10-6/h1-3H,(H,10,11)

Upstream product

• 76179-40-3 2-amino-4,5-difluoroaniline 
• 123-06-8 Ethoxymethylenemalononitrile 
• 124-38-9 carbon dioxide 
• 95-20-5 2-methyl-1H-indole 
• 215734-58-0 6,7-Difluoroquinoxaline 
• 68-12-2 N,N-dimethyl-formamide 
• 122-51-0 orthoformic acid triethyl ester 
• 64-18-6 formic acid 

Downstream Products

• 846049-02-3 4'-[(5,6-difluoro-1H-benzoimidazol-2-yl)-piperidin-4-ylidene-methyl]-biphenyl-3-carbonitrile 
• 846049-61-4 4-[(4-bromo-phenyl)-(5,6-difluoro-1H-benzoimidazol-2-yl)-methylene]-piperidine-1-carboxylic acid tert-butyl ester 
• 903899-03-6 4-[(4-bromo-phenyl)-(5,6-difluoro-1H-benzoimidazol-2-yl)-hydroxy-methyl]-piperidine-1-carboxylic acid tert-butyl ester 
• 279231-43-5 5,6-difluoro-1-methyl-1H-benzo[d]imidazole 

Relevant academic research and scientific papers

Di- and Trifluorinated 2-Azidobenzimidazole Derivatives: Synthesis, Photooxygenation, and 19F NMR Prediction

The photoreactivity of a series of hitherto unknown, multiply fluorinated 2-azidobenzimidazole derivatives was investigated. The synthesis of the starting material includes regioselective p-defluorination of nitrobenzene derivatives employing Ogoshi's conditions. If the 6-position was unsubstituted, irradiation in the presence of N-protected amino acids at 300 nm (Rayonet) led to the formation of arylesters by oxygenation of the 6-position in good to excellent yields and perfect regioselectivity. We did not observe any displacement of fluoride. If the 6-position itself was fluorinated, alternative positions of the benzene portion were attacked. Mechanistically, the reaction proceeds through ring opening of the singlet nitrene to the cyanodiimine or via the iminobenzimidazolium ion. The availability of a set of fluorinated photo-adducts prompted the quantum chemical calculation of their 19F NMR chemical shifts. Even with the most suitable method investigated (ωB97XD/TApr-cc-pVDZ), deviations of up to 5 ppm from the experimental values were observed, underlining the importance of experimental measurements.

In Situ Formation of Frustrated Lewis Pairs in a Water-Tolerant Metal-Organic Framework for the Transformation of CO2

Frustrated Lewis pairs (FLPs) consist of sterically hindered Lewis acids and Lewis bases, which provide high catalytic activity towards non-metal-mediated activation of “inert” small molecules, including CO2 among others. One critical issue of homogeneous FLPs, however, is their instability upon recycling, leading to catalytic deactivation. Herein, we provide a solution to this issue by incorporating a bulky Lewis acid-functionalized ligand into a water-tolerant metal-organic framework (MOF), named SION-105, and employing Lewis basic diamine substrates for the in situ formation of FLPs within the MOF. Using CO2 as a C1-feedstock, this combination allows for the efficient transformation of a variety of diamine substrates into benzimidazoles. SION-105 can be easily recycled by washing with MeOH and reused multiple times without losing its identity and catalytic activity, highlighting the advantage of the MOF approach in FLP chemistry.

Efficient N-Heterocyclic Carbene/Ruthenium Catalytic Systems for the Alcohol Amidation with Amines: Involvement of Poly-Carbene Complexes?

The atom-economic direct amidation of alcohols with amines has been recently highlighted as an attractive and promising transformation. Among the versatile reported catalytic systems, in situ generated N-heterocyclic carbene (NHC)/ruthenium (Ru) catalytic systems have demonstrated their advantages such as easy operation and use of commercial Ru compounds. However, the existing catalyst loadings are relatively high, and additional insights for the in situ catalyst generation are still not well-documented. In this work, a variety of benzimidazole-based NHC precursors were initially synthesized. Through the screening of various NHC precursors and other reaction conditions, active in situ catalytic systems were discovered for the efficient amide synthesis. Notably, the catalyst loading is as low as 0.5 mol %. Furthermore, additional experiments were performed to validate the rationale for the superiority of the current catalytic systems over our previous system. It was observed that the ligand structure is one of the reasons for the higher activity. In addition, the higher ratio of the NHC precursor/[Ru] is another important factor for the improvement. Further HR-MS analysis identified the formation of two mono-NHC-Ru species as major species and two Ru species bearing multiple NHC ligands as minor species. Hopefully, the efficient and readily-accessible catalytic systems reported herein could demonstrate great potential for further practical applications.

Transformations of 6,7-difluoroquinoxaline with Indoles: Synthesis of Indole-Substituted 6,7-difluoroquinoxalines and Tris(indol-3-yl)methane Derivatives

6,7-Difluoroquinoxaline (1) reacted with 1- and 2-methylindoles (2a and 2b) with heating in AcOH to give products from substitution of H in the heterocyclic fragment (3a and 3b) and tris(indol-3-yl)methane derivatives (4a and 4b).

Synthesis of benzimidazoles from o-phenylenediamines and DMF derivatives in the presence of PhSiH3

A simple approach to preparation of benzimidazoles from o-phenylenediamines and DMF derivatives, only employing PhSiH3 as promoter without any other additives, was reported. This route provided moderate to high yields with a broad substrate scope. A plausible mechanism for the reaction is proposed based on the spectroscopic characterization (e.g., HRMS and 1H NMR) of the reaction mixture.

HETEROCYCLIC COMPOUNDS AND USE THEREOF AS MODULATORS OF TYPE III RECEPTOR TYROSINE KINASES

Provided herein are heterocyclic compounds for treatment of CSF1R, FLT3, KIT, and/or PDGFRβ kinase mediated diseases. Also provided are pharmaceutical compositions comprising the compounds and methods of using the compounds and compositions.

NEW SUBSTITUTED BIPHENYL ANALOGUES AS DUAL INHIBITORS OF AROMATASE AND SULFATASE

Provided are new biphenyl derivatives of formula (Ia). These compounds act as aromatase and sulfatase inhibitors. They are particularly useful for treating pathological conditions or diseases in which aromatase and sulfatase are involved. Moreover, provided are processes for the preparation of these compounds and pharmaceutical compositions containing said products and their use for the preparation of a medicament, in particular for the treatment of diseases characterized by aromatase and sulfatase activity such as hormone-dependent cancers.

Chemo-enzymatic synthesis and biological evaluation of 5,6-disubstituted benzimidazole ribo- and 2′-deoxyribonucleosides

A number of new 5,6-disubstituted benzimidazoles have been prepared and their substrate properties for recombinant E. coli purine nucleoside phosphorylase (PNP; the product of the deoD gene) in the transglycosylation reaction were investigated. The heterocyclic bases showed good substrate activity for PNP and the ribo- and 2-deoxyribonucleosides were synthesized. The predominant (OMe and OEt) or exclusive (Oi-Pr, morpholino, and N-methylpiperazino) formation of the 5-substituted 6-fluoro-1-(β-d- ribofuranosyl)benzimidazoles was observed. The formation of the regioisomeric 6- methoxy-, 6-ethoxy-, or 6-isopropoxy-substituted 1-(2-deoxy-β-d- ribofuranosyl)-5-fluorobenzimidazoles was observed in the trans-2- deoxyribosylation reaction of the corresponding bases. The predominant or exclusive formation of the regioisomeric N1-nucleosides with bulky 5-substituents of 6-fluorobenzimidazole points to a large hydrophobic pocket in the E. coli PNP active site that can accommodate these groups. The biological activity of the synthesized nucleosides was studied and revealed no inhibitory activity against a broad variety of DNA and RNA viruses. The compounds also lacked significant cytotoxicity. Georg Thieme Verlag Stuttgart New York.

7-Substituted Purine Derivatives for Immunosuppression

The present invention provides novel purinone and related derivatives useful for the prevention and treatment of autoimmune diseases, inflammatory disease, mast cell mediated disease and transplant rejection. The compounds are of the general formula III:

7-SUBSTITUTED PURINE DERIVATIVES FOR IMMUNOSUPPRESSION

The present invention provides novel purinone and related derivatives useful for the prevention and treatment of autoimmune diseases, inflammatory disease, mast cell mediated disease and transplant rejection. The compounds are of the general formula (III).