57182-49-7

Basic information

• Product Name: 2-[(4-methylphenyl)amino]naphthalene-1,4-dione
• CAS NO: 57182-49-7
• Molecular Formula: C₁₇H₁₃NO₂
• Molecular Weight: 263.2906
• Mol File: 57182-49-7.mol
• Article Data: 20

Chemical Properties

• Boiling Point: 432.3°C at 760 mmHg
• Flash Point: 166.6°C
• Density: 1.304g/cm³
• Vapor Pressure: 1.12E-07mmHg at 25°C
• Refractive Index: 1.688
• CAS DataBase Reference: 2-[(4-methylphenyl)amino]naphthalene-1,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[(4-methylphenyl)amino]naphthalene-1,4-dione(57182-49-7)
• EPA Substance Registry System: 2-[(4-methylphenyl)amino]naphthalene-1,4-dione(57182-49-7)

Safety Data

• Hazardous Substances Data: 57182-49-7(Hazardous Substances Data)

Usage

Molecular structure

The compound has a naphthalene-1,4-dione backbone with an attached 4-methylphenylamino group.

Usage

It is commonly used in the synthesis of dyes and pigments, as well as in the production of optical brighteners and fluorescent dyes.

Industrial applications

It has potential uses in organic electronic devices and as a sensitizer in dye-sensitized solar cells.

Biological activities

It has been studied for its potential anti-cancer and anti-inflammatory properties.

Wide range of applications

The compound has a variety of uses and potential applications in different industries.

Upstream product

• 83-72-7 2-hydroxynaphtho-1,4-quinone 
• 106-49-0 p-toluidine 
• 130-15-4 [1,4]naphthoquinone 
• 110-86-1 pyridine 
• 117-80-6 2,3-Dichloro-1,4-naphthoquinone 
• 2348-82-5 2-methoxy-1,4-naphthoquinone 
• 90-15-3 α-naphthol 
• 2065-37-4 2-bromo-1,4-naphthoquinone 
• 99-99-0 1-methyl-4-nitrobenzene 
• 91-20-3 naphthalene 
• 524-42-5 1,2-naphthoquinone 
• 36417-25-1 2-hydroxy-1,4-naphthoquinone silver salt 
• 2066-93-5 3,4-dioxo-3,4-dihydro-naphthalene-1-sulfonic acid 
• 64-17-5 ethanol 

Downstream Products

• 64505-84-6 2-bromo-3-(p-tolylamino)naphthalene-1,4-dione 
• 1445727-17-2 2-(prop-2-ynyl(p-tolyl)amino)naphthalene-1,4-dione 
• 1445727-31-0 1-p-tolyl-1,2-dihydrobenzo[g]quinoline-5,10-dione 

Relevant articles and documents

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.

Photoinduced EDA Complexes Enabled Radical Tandem Cyclization/Arylation of Unactivated Alkene with 2-Amino-1,4-naphthoquinones

A visible-light-induced radical tandem cyclization/arylation between 2-amino-1, 4-naphthoquinone and N-allyl-2-bromo-2,2-difluoroacetamides has been developed without an external photocatalyst. The transformation could be carried out at room temperature a

A One-Pot Approach to 2-(N-Substituted Amino)-1,4-naphthoquinones with Use of Nitro Compounds and 1,4-Naphthoquinones in Water

A one-pot synthesis of 2-(N-substituted amino)-1,4-naphthoquinones from 1,4-naphthoquinones and nitro compounds in water has been developed. This method features mild reaction conditions and provides aromatic nitro compounds with various functional groups such as halogens, methylthio, ester, amide, even allyl, propargyl, and heterocycles, as well as aliphatic nitro compounds that are well tolerated. This method can be scaled up and we conducted further transformation of the obtained 2-(N-substituted amino)-1,4-naphthoquinones to synthesize carbazolequinone derivatives.