23008-56-2

Usage

Uses

Used in Pharmaceutical Industry:
N-(4-CHLOROPHENYL)-2-NITROBENZENAMINE is used as a reagent for the synthesis of novel 4-phenoxyquinoline derivatives, which serve as c-Met kinase inhibitors. These inhibitors play a crucial role in the development of targeted therapies for various diseases, including cancer.
Used in Chemical Synthesis:
N-(4-CHLOROPHENYL)-2-NITROBENZENAMINE is also used as an intermediate in the synthesis of Clofazimine, an anti-mycobacterial drug used to treat leprosy and other mycobacterial infections.
Used in Textile Industry:
In the textile industry, N-(4-CHLOROPHENYL)-2-NITROBENZENAMINE is used as a dye for coloring fabrics. It offers properties such as:
Standard Vinegar Fiber: The dye is compatible with standard vinegar fiber, which is commonly used in the textile industry.
Ironing Fastness: The color remains fast even after ironing, ensuring the fabric's appearance is maintained during use.
Light Fastness: The dye is resistant to fading under direct sunlight, making it suitable for outdoor applications.
Perspiration Fastness: The color does not fade or stain when exposed to sweat, making it ideal for clothing that requires frequent washing.
Washing Fastness: The dye is resistant to fading and staining during the washing process, ensuring the fabric's color remains vibrant even after multiple washes.
ISO Standards:
N-(4-CHLOROPHENYL)-2-NITROBENZENAMINE meets the following ISO standards for colorfastness:
These standards ensure the quality and performance of the dye in various applications within the textile industry.

Preparation

4-Chlorobenzenamine and 1-Chloro-2-nitrobenzene?condensation

StandardVinegar fiber

Ironing Fastness

Fading

Stain

Upstream product

• 119-75-5 2-nitro-N-phenylaniline 
• 127-09-3 sodium acetate 
• 106-47-8 4-chloro-aniline 
• 88-73-3 2-Chloronitrobenzene 
• 1493-27-2 ortho-nitrofluorobenzene 
• 15163-59-4 potassium o-nitrobenzoate 
• 5570-19-4 2-nitrophenylboronic acid 

Downstream Products

• 68817-71-0 2-(4-chloroanilino)aniline 
• 99979-13-2 (4-chloro-phenyl)-(2-nitro-phenyl)-nitroso-amine 
• 97870-46-7 1-(4-chlorophenyl)-2-propylbenzimidazole 
• 1381841-38-8 C₁₈H₁₈ClN₃ 
• 22316-22-9 1-(4-chlorophenyl)-1H-benzo[b][1,4]diazepine-2,4(3H,5H)-dione 
• 1407832-61-4 1-(4-chlorophenyl)-4-thioxo-4,5-dihydro-1H-benzo[b][1,4]diazepin-2(3H)-one 
• 1407832-63-6 6-(4-chlorophenyl)-1-methyl-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepin-5(6H)-one 
• 1407833-23-1 ethyl 1-(4-chlorophenyl)-2,4-dioxo 1,2,4,5-tetrahydrospiro[benzo[b][1,4]diazepine-3,1'-cyclopropane]-2'-carboxylate 
• 1407833-27-5 ethyl 1-(4-chlorophenyl)-2-oxo-4-thioxo-1,2,4,5-tetrahydrospiro[benzo[b][1,4]diazepine-3,1'-cyclopropane]-2'-carboxylate 
• 1407833-30-0 ethyl 6-(4-chlorophenyl)-1-methyl-5-oxo-5,6-dihydrospiro[benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepine-4,1'-cyclopropane]-2'-carboxylate 
• 1407833-34-4 6-(4-chlorophenyl)-1-methyl-5-oxo-5,6-dihydrospiro[benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepine-4,1'-cyclopropane]-2'-carboxylic acid 
• 1407832-65-8 6-(4-chlorophenyl)-1,4-dimethyl-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepin-5(6H)-one 
• 1407833-68-4 6-(4-chlorophenyl)-4-ethyl-1-methyl-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepine-5(6H)-one 
• 1407829-45-1 6-(4-chlorophenyl)-1,4-dimethyl-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepine 

Relevant academic research and scientific papers

Antitubercular agents. Part 1: Synthesis of phthalimido- and naphthalimido-linked phenazines as new prototype antitubercular agents

The preparation and antitubercular properties of a series of phthalimido- and naphthalimido-linked phenazines are described. Some of these new compounds inhibited the growth of Mycobacterium tuberculosis ATCC 27294, Mycobacterium avium ATCC 49601, Mycobacterium intracellulare ATCC 13950 and some clinical isolates.

An efficient and fast procedure for the preparation of 2-nitrophenylamines under microwave conditions

2-Nitrophenylamines were prepared in good yields from 2-chloronitrobenzen (or 2-fluoronitrobenzene) and amines in the presence of anhydrous potassium fluoride under microwave irradiation and solvent free conditions.

Design, synthesis, and biological evaluation of benzo[d]imidazole-2-carboxamides as new anti-TB agents

Tuberculosis is the leading cause of death globally among infectious diseases. Due to the development of resistance of Mycobacterium tuberculosis to currently used anti-TB medicines and the TB-HIV synergism the urgent need to develop novel anti-mycobacterial agents has been realized. The drug-to-target path has been the successful strategy for new anti-TB drug development. All the six drug candidates that have shown promise during the clinical trials and some of these being approved for treatment against MDR TB are the results of phenotype screening of small molecule compound libraries. In search of compounds belonging to novel pharmacophoric class that could be subjected to whole cell assay to generate new anti-TB leads the benzo[d]imidazole-2-carboxamide moiety has been designed as a novel anti-TB scaffold. The design was based on the identification of the benzimidazole ring as a prominent substructure of the FDA approved drugs, the structural analysis of reported anti-TB benzimidazoles, and the presence of the C-2 carboxamido functionality in novel bioisoteric anti-TB benzothiazoles. Twenty seven final compounds have been prepared via NH4Cl-catalyzed amidation of ethyl benzo[d]imidazole-2-carboxylates, as the required intermediates, obtained through a green “all water” one-pot synthetic route following a tandem N-arylation-reduction-cyclocondensation procedure. All of the synthesised target compounds were assessed for anti-TB potential using H37Rv ATCC27294 strain. Thirteen compounds were found with better MIC (0.78–6.25 μg/mL) than the standard drugs and being non-cytotoxic nature ( 60) and a few others e.g., 8a, 8f, 8k and 8o are the next best anti-TB hits (MIC: 1.56 μg/mL). The determination and analysis of various physiochemical parameters revealed favorable druglike properties of the active compounds. The compounds 8a-l and 8o, with MIC values of ≤ 6.25 μg/mL, have high LipE values (10.66–11.77) that are higher than that of the suggested value of > 6 derived from empirical evidence for quality drug candidates and highlight their therapeutic potential. The highest LipE value of 11.77 of the best active compound 8e with the MIC of 0.78 μg/mL indicates its better absorption and clearance as a probable clinical candidate for anti-TB drug discovery. These findings highlight the discovery of benzimidazole-2-carboxamides for further development as new anti-TB agents.

A green and practical reduction of N-(4-chlorophenyl)-2-nitroaniline and its derivatives to corresponding N-substituted-benzene-1,2-diamines using thiourea dioxide

A new effective approach for synthesizing diverse N-substituted-benzene-1,2-diamines is reported. The treatment of N-substituted-2-nitroanilines with thiourea dioxide in the presence of sodium hydroxide efficiently formed the corresponding N-substituted-benzene-1,2-diamines, including N-(4-chlorophenyl)benzene-1,2-diamine with a good yield of 94%. The by-product is environmentally-friendly urea and is easy to separate from the product by filtration procedure that enhances the convenience of the approach.

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.

Decarboxylative ipso Amination of Activated Benzoic Acids

In the presence of a bimetallic Pd/Cu system with 1,10-phenanthroline as the ligand and either air or N-methylmorpholine N-oxide as the oxidant, electron-deficient benzoic acids undergo oxidative decarboxylative coupling with unprotected amines. This operationally simple aniline synthesis is widely applicable with respect to the amine and gives good yields, even on multigram scale. The orthogonality of this reaction to other Pd-catalyzed cross-couplings allows the concise synthesis of multisubstituted arenes by sequential C?C, C?Cl, and C?N functionalizations. Mechanistic investigations suggest the intermediacy of a hypervalent Pd species.

Selenium-Catalyzed Carbonylative Synthesis of 2-Benzimidazolones from 2-Nitroanilines with TFBen as the CO Source

A selenium-catalyzed carbonylative reaction for the synthesis of 2-benzimidazolones from 2-nitroanilines has been developed. In this strategy, to avoid the usage of toxic CO gas, TFBen (benzene-1,3,5-triyl triformate) was used as a solid and stable CO precursor, and a variety of desired 2-benzimidazolones were produced in moderate to excellent yields.

Preparation and characterization of isatin complexed with Cu supported on 4-(aminomethyl) benzoic acid-functionalized Fe3O4 nanoparticles as a novel magnetic catalyst for the Ullmann coupling reaction

Isatin complexed with Cu supported on 4-(aminomethyl) benzoic acid-functionalized Fe3O4 nanoparticles (Cu-IS-AMBA-MNPs) as a new catalyst was designed, prepared and characterized by appropriate analyses. The heterogeneous reusable catalyst was successfully used for the efficient and widespread syntheses of diaryl ethers and diarylamines via the Ullmann coupling reaction. This green catalyst was easily removed, reused several times with no significant loss of its activity, and provided a clean synthesis with excellent yield and reduced time.

Preparation method for clofazimine intermediate

The invention relates to a preparation method for a clofazimine intermediate N-(4-chlorophenyl)-2-nitrobenzene as shown in a formula III which is described in the specification. The preparation method is simple and safe to operate, good in yield, small in environmental pollution, excellent in economic effect and suitable for industrial production.

Design, synthesis and biological evaluation of novel 4-phenoxyquinoline derivatives containing 3-oxo-3,4-dihydroquinoxaline moiety as c-Met kinase inhibitors

A series of novel 4-phenoxyquinoline derivatives containing 3-oxo-3,4-dihydroquinoxaline moiety were synthesized and evaluated for their c-Met kinase inhibitory activity and antiproliferative activity against five cancer cell lines (HT-29, H460, A549, MKN-45 and U87MG) in vitro. Most of the compounds exhibited moderate-to-significant cytotoxicity as compared with foretinib. The most promising compound 41 (with c-Met IC50 value of 0.90?nM) showed remarkable cytotoxicity against HT-29, H460, A549, MKN-45 and U87MG cell lines with IC50 values of 0.06?μM, 0.05?μM, 0.18?μM, 0.023?μM and 0.66?μM, respectively, and thus it was 1.22- to 3.50-fold more potent than foretinib. Their preliminary structure-activity relationships (SARs) studies indicate that electron-withdrawing groups on the terminal phenyl rings are beneficial for improving the antitumor activity.