3144-89-6

Usage

Physical Form

Bright yellow powder

Molecular Weight

319.753 g/mol

Usage

Commonly used as a dye in the textile industry

Applications

Dyeing wool, silk, and textiles, as well as in the production of ink, paint, and plastics

Safety Precautions

Skin and eye irritant, should be used in well-ventilated areas to prevent inhalation.

InChI:InChI=1/C16H10ClNO2/c17-10-5-7-11(8-6-10)18-14-9-15(19)12-3-1-2-4-13(12)16(14)20/h1-9,18H

Upstream product

• 110-86-1 pyridine 
• 117-80-6 2,3-Dichloro-1,4-naphthoquinone 
• 106-47-8 4-chloro-aniline 
• 130-15-4 [1,4]naphthoquinone 
• 2348-82-5 2-methoxy-1,4-naphthoquinone 
• 83-72-7 2-hydroxynaphtho-1,4-quinone 
• 2065-37-4 2-bromo-1,4-naphthoquinone 
• 75112-58-2 2-(4-chloroanilino)-1,4-naphthoquinone-3-pyridinium chloride 
• 6373-23-5 4-((4-chlorophenyl)amino)naphthalene-1,2-dione 

Downstream Products

• 64505-81-3 2-chloro-3-(4-chlorophenylamino)naphthalene-1,4-dione 
• 868562-64-5 C₃₂H₁₈Cl₂N₂O₄S₂ 
• 128475-23-0 N-methyl-2-(4-chlorophenyl)amino-1,4-naphthoquinone 
• 1445727-19-4 2-((4-chlorophenyl)(prop-2-ynyl)amino)naphthalene-1,4-dione 
• 1445727-30-9 2-((4-chlorophenyl)(pent-2-ynyl)amino)naphthalene-1,4-dione 
• 1445727-33-2 1-(4-chlorophenyl)-1,2-dihydrobenzo[g]quinoline-5,10-dione 
• 1445727-44-5 1-(4-chlorophenyl)-4-ethyl-1,2-dihydrobenzo[g]quinoline-5,10-dione 

Relevant academic research and scientific papers

Isomerization of 4-arylamino-1,2-naphthoquinones to 2-arylamino-1,4-naphthoquinones

4-Arylamino-1,2-naphthoquinones isomerize into 2-arylamino-1,4-naphthoquinones upon refluxing in acetic acid. The isomerization follows two routes via intermediate 2-hydroxy-1,4-naphthoquinone and 2-arylamino-1,4-naphthoquinone 4-N-arylimines.

General method for the high yield preparation of 2-(4-X-phenylene)amine-1,4-naphthoquinones (X = ferrocenyl, OMe, Me, I, Cl, and NO2) from 2-methoxy-1,4-naphthoquinone and investigation of H+ and Mg2+ catalysts with DFT calculations

A rapid and simple method for the high yield preparation of 2-(4-X-phenylene)amine-1,4-naphthoquinones from 2-methoxy-1,4-naphthoquinone, in boiling MeOH, using MgCl2 and p-toluenesulfonic acid as catalysts is described. This methodology has been applied successfully to the synthesis of electron donor (4-OMe, 4-Me, 4-ferrocenyl) and electron withdrawing (4-I, 4-Cl, 4- and 3-NO2) aniline derivatives. The effect of both H+ and Mg2+ as catalysts was investigated using DFT calculations carried out at the B3LYP/6-31G(d) level. The electronic properties of the novel 2-(4-ferrocenylphenylene)amine-1,4-naphthoquinone 3b were investigated and show that the ferrocenyl and the methoxy group have similar electron donor properties in 2-(4-methoxy)amine-1,4-naphthoquinone 3a.

Exploration of Benzo[b]carbazole-6,11-diones as anticancer agents: Synthesis and studies of hTopoIIα inhibition and apoptotic effects

Two series of (hetero)arylamino-naphthoquinones and benzo-fused carbazolequinones were considered for study with the rationale that related structural motifs are present in numerous drugs, clinical trial agents, natural products and hTopoIIα inhibitors. Total 42 compounds were synthesized by reactions including dehydrogenative C–N and Pd-catalyzed C–C bond forming transformations. These compounds were screened against numerous cancer cells including highly metastatic one (MCF-7, MDA-MB-231, H-357 and HEK293T), and normal cells (MCF 10A). Some of the active compounds were evaluated for clonogenic cell survival and apoptotic effects in cancer cells (DAPI nuclear staining, Comet assay, Annexin-V-FITC/PI dual staining, flow cytometry, and western blot analysis with relevant proteins). All compounds were tested for hTopoIIα inhibitory activity. The investigated series compounds showed important properties like significant apoptotic antiproliferation in cancer cells with cell cycle arrest at S-phase and downregulation of NF- κβ signaling cascade, relatively less cytotoxicity to normal cells, and hTopoIIα inhibition with more efficiency compared to an anticancer drug etoposide.

Fluorescent 1,4-Naphthoquinones to Visualize Diffuse and Dense-Core Amyloid Plaques in APP/PS1 Transgenic Mouse Brains

Recent clinical approvals of brain imaging radiotracers targeting amyloid-β provided clinicians the tools to detect and confirm Alzheimer's disease pathology without autopsy or biopsy. While current imaging agents are effective in postsymptomatic Alzheimer's patients, there is much room for improvement in earlier diagnosis, hence prompting a need for new and improved amyloid imaging agents. Here we synthesized 41 novel 1,4-naphthoquinone derivatives and initially discovered 14 antiamyloidogenic compounds via in vitro amyloid-β aggregation assay; however, qualitative analyses of these compounds produced conflicting results and required further investigation. Follow-up docking and biophysical studies revealed that four of these compounds penetrate the blood-brain barrier, directly bind to amyloid-β aggregates, and enhance fluorescence properties upon interaction. These compounds specifically stain both diffuse and dense-core amyloid-β plaques in brain sections of APP/PS1 double transgenic Alzheimer's mouse models. Our findings suggest 1,4-naphthoquinones as a new scaffold for amyloid-β imaging agents for early stage Alzheimer's.

Synthesis of novel substituted methoxybenzo[2,3-b]carbazole derivatives via C-H functionalization. Experimental and theoretical characterization of their photophysical properties

The novel, highly blue, fluorescent N-methyl-6,11-dimethoxybenzo[2,3-b]carbazole derivatives were prepared by oxidative coupling of anilines with naphthoquinone followed by palladium catalyzed oxidative [Formula presented] functionalization and a one pot

INHIBITORS OF THE MITF MOLECULAR PATHWAY

Provided herein are compounds of the formula (IV) as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful as MITF inhibitors, MITF pathway inhibitors and for the treatment of cancer.

An expedient synthesis of 1,2-dihydrobenzo[g]quinoline-5,10-diones via copper(II) triflate-catalyzed intramolecular cyclization of N- propargylaminonaphthoquinones

An expedient synthesis of a series of 1,2-dihydrobenzo[g]quinoline-5,10- diones in good yields has been accomplished via three-component one pot sequential reactions of 2-hydroxynaphthalene-1,4-dione, substituted anilines and propargyl as well as 3-ethylp

Bodipy derivatives as organic triplet photosensitizers for aerobic photoorganocatalytic oxidative coupling of amines and photooxidation of dihydroxylnaphthalenes

We used iodo-Bodipy derivatives that show strong absorption of visible light and long-lived triplet excited states as organic catalysts for photoredox catalytic organic reactions. Conventionally most of the photocatalysts are based on the off-the-shelf compounds, usually showing weak absorption in the visible region and short triplet excited state lifetimes. Herein, the organic catalysts are used for two photocatalyzed reactions mediated by singlet oxygen ( 1O2), that is, the aerobic oxidative coupling of amines and the photooxidation of dihydroxylnaphthalenes, which is coupled to the subsequent addition of amines to the naphthoquinones, via C-H functionalization of 1,4-naphthoquinone, to produce N-aryl-2-amino-1,4-naphthoquinones (one-pot reaction), which are anticancer and antibiotic reagents. The photoreactions were substantially accelerated with these new iodo-Bodipy organic photocatalysts compared to that catalyzed with the conventional Ru(II)/Ir(III) complexes, which show weak absorption in the visible region and short-lived triplet excited states. Our results will inspire the design and application of new organic triplet photosensitizers that show strong absorption of visible light and long-lived triplet excited state and the application of these catalysts in photoredox catalytic organic reactions.

C-H functionalization of 1,4-naphthoquinone by oxidative coupling with anilines in the presence of a catalytic quantity of copper(II) acetate

The oxidative addition of anilines (2) with 1,4-naphthoquinone (3) to give N-aryl-2-amino-1,4-naphthoquinones (1) was found to be catalyzed by copper(II) acetate. In the absence of the catalyst, the reactions are slower and give lower yields with the formation of many colateral products. In the presence of 10 mol % hydrated copper(II) acetate, the reactions are generally more efficient in that they are cleaner, higher yielding, and faster.

Sulfur-containing derivatives of 1,4-naphthoquinone, part 1: Disulfide synthesis

Bisulfides of 1,4-naphthoquinone were synthesized, and different methods of their synthesis were investigated. High yields and purity of disulfides were obtained from the oxidation of thiol derivatives. The latter were prepared in high yields and purity from isothiuronic salts. The obtained disulfides are synthones for compounds with a wide spectrum of biological activity.