2369-29-1

Usage

Uses

Used in Chemical Synthesis:
1,2-Diamino-3,5-difluorobenzene is used as a building block for the synthesis of more complex chemical structures. Its unique combination of amine and fluoride groups allows for versatile reactivity in various chemical reactions, making it a valuable intermediate in the production of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
1,2-Diamino-3,5-difluorobenzene is used as a key intermediate in the development of new pharmaceutical compounds. Its presence in the molecular structure can influence the properties of the final drug, such as solubility, stability, and bioavailability, which are crucial for the drug's effectiveness and safety.
Used in Agrochemical Industry:
1,2-Diamino-3,5-difluorobenzene is used as a starting material in the synthesis of agrochemicals, such as pesticides and herbicides. The introduction of fluorine atoms can enhance the lipophilicity and metabolic stability of these compounds, leading to improved performance in agricultural applications.
Used in Research and Development:
1,2-Diamino-3,5-difluorobenzene is used as a research compound in academic and industrial laboratories. Its unique structure and reactivity make it an interesting subject for studies in organic chemistry, materials science, and related fields, contributing to the advancement of scientific knowledge and the development of new technologies.

InChI:InChI=1/C6H6F2N2/c7-3-1-4(8)6(10)5(9)2-3/h1-2H,9-10H2

Upstream product

• 372-39-4 3,5-difluoroaniline 
• 364-78-3 2-nitro-4-fluoroaniline 
• 399-36-0 N-(2,4-difluoro-phenyl)-acetamide 
• 2368-53-8 1,3-dichloro-2,4,6-trifluorobenzene 
• 364-30-7 2-amino-3,5-difluoronitrobenzene 

Downstream Products

• 1221793-66-3 4,6-difluoro-1H-benzo[d]imidazol-2-(3H)-one 
• 2208-24-4 4,6-difluoro-1H-benzimidazole 
• 394222-91-4 (4,6-Difluoro-1H-benzimidazol-2-yl)-methylamine 
• 435281-21-3 1-(2-amino-4,6-difluorophenyl)-3-(2,6-dichlorophenyl)thiourea 
• 439-17-8 5,7-difluoro-2,3-diphenyl-quinoxaline 
• 1163728-92-4 2-[4-(1H-[1,2,4]-triazol-1-yl)phenyl]-4,6-difluoro-1H-benzo[d]imidazole 

Relevant academic research and scientific papers

Regioselective Radical Arene Amination for the Concise Synthesis ofortho-Phenylenediamines

The formation of arene C-N bonds directly from C-H bonds is of great importance and there has been rapid recent development of methods for achieving this through radical mechanisms, often involving reactiveN-centered radicals. A major challenge associated with these advances is that of regiocontrol, with mixtures of regioisomeric products obtained in most protocols, limiting broader utility. We have designed a system that utilizes attractive noncovalent interactions between an anionic substrate and an incoming radical cation in order to guide the latter to the areneorthoposition. The anionic substrate takes the form of a sulfamate-protected aniline and telescoped cleavage of the sulfamate group after amination leads directly toortho-phenylenediamines, key building blocks for a range of medicinally relevant diazoles. Our method can deliver both free amines and monoalkyl amines allowing access to unsymmetrical, selectively monoalkylated benzimidazoles and benzotriazoles. As well as providing concise access to valuableortho-phenylenediamines, this work demonstrates the potential for utilizing noncovalent interactions to control positional selectivity in radical reactions.

Chemoenzymatic Synthesis and Antiherpes Activity of 5-Substituted 4,6-Difluorobenzimidazoles Ribo- and 2′-Deoxyribonucleosides

A series of 5,6-disubstituted benzimidazole nucleosides, obtained earlier, did not show any significant antiviral activity at relatively low cytotoxicity in vitro. In the course of our research we have succeeded in introducing an additional fluorine atom

SAR156497, an exquisitely selective inhibitor of Aurora kinases

The Aurora family of serine/threonine kinases is essential for mitosis. Their crucial role in cell cycle regulation and aberrant expression in a broad range of malignancies have been demonstrated and have prompted intensive search for small molecule Auror

INHIBITORS OF FATTY ACID BINDING PROTEIN

The present invention relates to novel heterocyclic compounds as Fatty Acid Binding Protein (“FABP”) inhibitors, pharmaceutical compositions comprising the heterocyclic compounds and the use of the compounds for treating or preventing a cardiovascular disease, a metabolic disorder, obesity or an obesity-related disorder, diabetes, dyslipidemia, a diabetic complication, impaired glucose tolerance or impaired fasting glucose.

SAR study of clubbed [1,2,4]-triazolyl with fluorobenzimidazoles as antimicrobial and antituberculosis agents

In the present study, a series of novel 2-[4-(1H-[1,2,4]-triazol-1-yl)phenyl]-1-substituted-4,6-difluoro-1H-benz o[d]imidazole derivatives are synthesized by the alkylation of 2-[4-(1H-[1,2,4]-triazol-1-yl)phenyl]-4,6-difluoro-1H-benzo[d]imidazole with substituted alkyl and aryl halides. The compounds were evaluated for their preliminary in-vitro antibacterial activity against Pseudomonas aeruginosa, Escherichia coli, Staphylococcus aureus, and Salmonella typhosa and then were screened for their antitubercular activity against Mycobacterium tuberculosis H37Rv strain by broth microdilution assay method. The antibacterial data suggested that the analogs with electronegative substituents emerged as promising antimicrobials. It was also observed that the promising antimicrobials have proved to be better antimycobacterials. Few of selected analogs are under further evaluation for secondary antitubercular screening, as they have shown better activity compared to rifampin.

Development of a scalable synthesis of a nonbasic inhibitor of the serine protease tryptase

A chromatography-free process for the synthesis of a bis(benzimidazole)difluoromethane inhibitor of the serine protease tryptase is described. This synthesis features the introduction of the gem-difluoro moiety using the electrophilic fluorinating reagent N-fluoro-bis(phenylsulfonimide) as well as the stepwise introduction of both benzimidazole rings. A protocol for the destruction of reactive, process-related substances produced in the synthesis is also presented.

Catalytic and noncatalytic ammonolysis of polyfluorinated 1,3-dichlorobenzenes

Reactions of 1,3-dichlorotetrafluorobenzene and 1,3-dichloro-2,4,6-trifluorobenzene with aqueous ammonia in the presence and in the absence of copper(I) salt lead to fluorine replacement by amino group in the para and ortho positions with respect to the chlorine atom. Ammonolysis of the resulting chloropolyfluoroanilines in the absence of a catalyst involves replacement of fluorine atom in the meta position with respect to the amino group. In the presence of copper(I) salt, catalytic aminodechlorination occurs at the para and ortho positions with respect to the amino group introduced in the first stage.

Substituted benzimidazoles, processes for their preparation, their use as medicaments, and medicaments comprising them

The invention relates to the use of compounds of formula I for the production of a medicament for the treatment of illnesses which can be influenced by inhibition of the Na+/H+ exchanger, and to a medicament comprising them. in which R1 to R9 have the meanings shown in the claims.

Structure-activity relationship of omeprazole and analogues as Helicobacter pylori urease inhibitors

Helicobacter pylori urease belongs to a family of highly conserved urea- hydrolyzing enzymes. A common feature of these enzymes is the presence of two Lewis acid nickel ions and a reactive cysteine residue in the active site. The H+/K+-ATPase inhibitor omeprazole is a prodrug of a sulfenamide which covalently modifies cysteine residues on the luminal side of the H+/K+- ATPase of gastric parietal cells. Omeprazole and eight analogues were selected based on their chemical, electronic, and kinetic properties, and each was incubated with viable H. pylori in phosphate-buffered saline at pH 7.4 for 30 min, after which 100 mM urea was added and the amount of ammonia formed analyzed after a further 10 min. Inhibition between 0% and 100% at a 0.1 mM concentration was observed for the different analogues and could be expressed as a function of the pK(a)-value of the pyridine, the pK(a)-value of the benzimidazole, the overall lipophilicity, and, most importantly, the rate of sulfenamide formation, in a quantitative structure-activity relationship. The inhibition was potentiated by a lower pH (favoring the formation of the sulfenamide) but abolished in the presence of β- mercaptoethanol (a scavenger of the sulfenamide). Structural analogues incapable of yielding the sulfenamide did not inhibit ammonia production. Treatment of Helicobacter felis-infected mice with 230 μmol/kg flurofamide b.i.d. for 4 weeks, known to potently inhibit urease activity in vivo, as a means of eradicating the infection, was tested and compared with the effect of 125 μmol/kg omeprazole b.i.d. for 4 weeks. Neither treatment proved efficacious.