28898-03-5

Basic information

• Product Name: N-(2-FLUOROPHENYL)-1,2-DIAMINOBENZENE
• Synonyms: N-(2-FLUOROPHENYL)-1,2-DIAMINOBENZENE;N1-(2-Fluorophenyl)benzene-1,2-diamine;2-[(2-Fluorophenyl)amino]aniline;N1-(2-Fluorophenyl)benzene-1,2-diamine, 2-Amino-2'-fluorodiphenylamine;2-AMino-2'-fluorodiphenylaMine;2-[(2-Fluorophenyl)amine]aniline
• CAS NO: 28898-03-5
• Molecular Formula: C₁₂H₁₁FN₂
• Molecular Weight: 202.23
• Mol File: 28898-03-5.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• CAS DataBase Reference: N-(2-FLUOROPHENYL)-1,2-DIAMINOBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2-FLUOROPHENYL)-1,2-DIAMINOBENZENE(28898-03-5)
• EPA Substance Registry System: N-(2-FLUOROPHENYL)-1,2-DIAMINOBENZENE(28898-03-5)

Safety Data

• Hazardous Substances Data: 28898-03-5(Hazardous Substances Data)

Usage

Description

N-(2-FLUOROPHENYL)-1,2-DIAMINOBENZENE, also known as 2-Amino-2''-fluorodiphenylamine, is an organic compound with a fluorophenyl group attached to a 1,2-diaminobenzene structure. It is characterized by its unique molecular structure, which includes a fluorine atom attached to a phenyl ring and two amine groups on the adjacent benzene ring. N-(2-FLUOROPHENYL)-1,2-DIAMINOBENZENE is known for its potential applications in various industries due to its chemical properties.

Uses

Used in Pharmaceutical Industry:
N-(2-FLUOROPHENYL)-1,2-DIAMINOBENZENE is used as an intermediate for the synthesis of fluorophenazines. These fluorophenazines are important compounds with a wide range of biological activities, including antimicrobial, antifungal, and anti-inflammatory properties. The presence of the fluorine atom in the molecule can enhance the pharmacokinetic properties of the resulting fluorophenazines, making them more effective as therapeutic agents.
Used in Chemical Synthesis:
In the field of chemical synthesis, N-(2-FLUOROPHENYL)-1,2-DIAMINOBENZENE serves as a versatile building block for the creation of various complex organic molecules. Its unique structure allows for further functionalization and modification, leading to the development of new compounds with potential applications in different industries, such as materials science, agrochemicals, and pharmaceuticals.
Used in Research and Development:
N-(2-FLUOROPHENYL)-1,2-DIAMINOBENZENE is also utilized in research and development for the exploration of new chemical reactions and synthetic pathways. Its unique structure and reactivity make it an interesting candidate for studying various organic reactions, such as cross-coupling, electrophilic aromatic substitution, and nucleophilic aromatic substitution. This research can lead to the discovery of new synthetic methods and the development of novel compounds with potential applications in various fields.

Upstream product

• 88-73-3 2-Chloronitrobenzene 
• 1493-27-2 ortho-nitrofluorobenzene 
• 348-54-9 2-Fluoroaniline 
• 28898-02-4 N-(2-Fluorophenyl)-2-nitrobenzeneamine 

Downstream Products

• 151385-64-7 2-fluoro-2'-(3-methylbut-1-yl)aminodiphenylamine 
• 151386-29-7 1-N-(2-cyclopentylethyl)-2,4-dioxo-5-N-(2-fluorophenyl)-3-phenylhydrazono-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine 
• 151620-16-5 1-N-(3,3-dimethylbut-1-yl)-2,4-dioxo-5-N-(2-fluorophenyl)-3-(phenyloxycarbonylamino)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine 
• 151385-68-1 1-N-(3,3-dimethylbut-1-yl)-2,4-dioxo-5-N-(2-fluorophenyl)-3-phenylhydrazono-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine 
• 153930-53-1 1-(2-cyclopentylethyl)-2,4-dioxo-5-(2-fluorophenyl)-3-isocyanato-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine 
• 151620-69-8 3-amino-1-N-(2-cyclopentylethyl)-2,4-dioxo-5-N-(2-fluorophenyl)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine 
• 151620-61-0 3-amino-1-N-(3,3-dimethylbut-1-yl)-2,4-dioxo-5-N-(2-fluorophenyl)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine 
• 153930-31-5 2,4-dioxo-5-N-(2-fluorophenyl)-3-isocyanato-1-N-(3-methylbut-1-yl)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine 

Relevant articles and documents

Design, synthesis and biological evaluation of novel 4-phenoxypyridine based 3-oxo-3,4-dihydroquinoxaline-2-carboxamide derivatives as potential c-Met kinase inhibitors

Blocking c-Met kinase activity by small-molecule inhibitors has been identified as a promising approach for the treatment of cancers. Herein, we described the design, synthesis, and biological evaluation of a series of 4-phenoxypyridine-based 3-oxo-3,4-dihydroquinoxaline derivatives as c-Met kinase inhibitors. Inhibitory activitives against c-Met kinase evaluation indicated that most of compounds showed excellent c-Met kinase activity in vitro, and IC50 values of ten compounds (23a, 23e, 23f, 23l, 23r, 23s, 23v, 23w, 23x and 23y) were less than 10.00 nM. Notably, three of them (23v, 23w and 23y) showed remarkable potency with IC50 values of 2.31 nM, 1.91 nM and 2.44 nM, respectively, and thus they were more potent than positive control drug foretinib (c-Met, IC50 = 2.53 nM). Cytotoxic evaluation indicated the most promising compound 23w showed remarkable cytotoxicity against A549, H460 and HT-29 cell lines with IC50 values of 1.57 μM, 0.94 μM and 0.65 μM, respectively. Furthermore, the acridine orange/ethidium bromide (AO/EB) staining, cell apoptosis assays by flow cytometry, wound-healing assays and transwell migration assays on HT-29 and/or A549 cells of 23w were performed. Especially compound 23w, which displayed potent antitumor, apoptosis induction and antimetastatic activity, could be used as a promising lead for further development. Meanwhile, their preliminary structure-activity relationships (SARs) were also discussed.

Synthesis and biological evaluation of novel pyrazole carboxamide with diarylamine-modi?ed scaffold as potent antifungal agents

Twenty-seven novel pyrazole carboxamides with diarylamine-modi?ed scaffold were designed, synthesized and characterized in detail via 1H NMR, 13C NMR, IR and ESI-HRMS. Preliminary bioassays showed that some of the target compounds exhibited good antifungal activity against Rhizoctonia solani, Rhizoctonia cerealis and Sclerotinia sclerotiorum. Among them, compound 9c-7 exhibited the highest antifungal activities against R. solani, R. cerealis and S. sclerotiorum in vitro with IC50 values of 0.013, 1.608 and 1.874?μg/mL, respectively. Notably, compound 9c-7 still presented the highest fungicidal activities against R. solani in vivo with an IC50 value of 22.21?μg/mL. Molecular docking simulation results reveal that compound 9c-7 binds well to the hydrophobic pockets of the receptor protein succinate dehydrogenase. This study suggests that compound 9c-7 could act as a potential fungicide to be used for further optimization.

Discovery of novel selective norepinephrine reuptake inhibitors: 4-[3-Aryl-2,2-dioxido-2,1,3-benzothiadiazol-1(3 H)-yl]-1-(methylamino)butan-2- ols (WYE-103231)

Structural modification of a virtual screening hit led to the identification of a new series of 4-[3-aryl-2,2-dioxido-2,1,3-benzothiadiazol- 1(3H)-yl]-1-(methylamino)butan-2-ols which are potent and selective inhibitors of the norepinephrine transporter over both the serotonin and dopamine transporters. One representative compound S-17b (WYE-103231) had low nanomolar hNET potency (IC50 = 1.2 nM) and excellent selectivity for hNET over hSERT (>1600-fold) and hDAT (>600-fold). S-17b additionally had a good pharmacokinetic profile and demonstrated oral efficacy in rat models of ovariectomized-induced thermoregulatory dysfunction and morphine dependent flush as well as the hot plate and spinal nerve ligation (SNL) models of acute and neuropathic pain.