71369-17-0

Basic information

• Product Name: 2-chloro-3-phenoxynaphthoquinone
• Synonyms: 2-chloro-3-phenoxynaphthoquinone
• CAS NO: 71369-17-0
• Molecular Formula: C₁₆H₉ClO₃
• Molecular Weight: 284.69386
• Mol File: 71369-17-0.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 383.4 °C at 760 mmHg
• Flash Point: 153.1 °C
• Appearance: /
• Density: 1.41 g/cm³
• Vapor Pressure: 4.4E-06mmHg at 25°C
• Refractive Index: 1.658
• CAS DataBase Reference: 2-chloro-3-phenoxynaphthoquinone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-chloro-3-phenoxynaphthoquinone(71369-17-0)
• EPA Substance Registry System: 2-chloro-3-phenoxynaphthoquinone(71369-17-0)

Safety Data

• Hazardous Substances Data: 71369-17-0(Hazardous Substances Data)

Usage

General Description

2-chloro-3-phenoxynaphthoquinone is a chemical compound that belongs to the family of naphthoquinone derivatives. It is a chlorinated derivative of phenoxynaphthoquinone and is commonly used as a reagent in organic synthesis. 2-chloro-3-phenoxynaphthoquinone has a naphthoquinone core with a chlorine atom at position 2 and a phenoxy group at position 3. Its chemical structure makes it suitable for reactions involving electrophilic substitution and oxidative coupling. 2-chloro-3-phenoxynaphthoquinone is often utilized in the production of dyes, pharmaceuticals, and agrochemicals due to its versatile reactivity and functional group compatibility. Additionally, it has been studied for its potential biological activities and pharmacological properties, making it a valuable target for medicinal chemistry research.

InChI:InChI=1/C16H9ClO3/c17-13-14(18)11-8-4-5-9-12(11)15(19)16(13)20-10-6-2-1-3-7-10/h1-9H

Upstream product

• 117-80-6 2,3-Dichloro-1,4-naphthoquinone 
• 108-95-2 phenol 
• 139-02-6 sodium phenoxide 

Downstream Products

• 380652-86-8 N-(1',4'-dioxo-3'-(phenylamino)-1',4'-dihydronaphthalen-2'-yl)benzenesulphonamide 
• 1218995-99-3 N-(3'-(3,5-dimetylphenylamino)-1',4'-dioxo-1',4'-dihydronaphthalen-2'-yl)benzenesulphonamide 
• 1218995-97-1 N-(3'-(4-bromophenylamino)-1',4'-dioxo-1',4'-dihydronaphthalen-2'-yl)benzenesulphonamide 
• 1301627-22-4 N-(3-((2-methoxyethyl)amino)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulfonamide 
• 1301627-24-6 N-(3-(cyclopentylamino)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulfonamide 
• 328035-98-9 N-(3-(benzylamino)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulfonamide 
• 1301626-89-0 N-(3-(2-chlorophenyl)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulfonamide 
• 1301626-91-4 N-(3-(3-chlorophenyl)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulfonamide 
• 1301626-92-5 N-(3-(4-chlorophenyl)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulfonamide 
• 1301626-93-6 N-(3-(3-formylphenyl)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulfonamide 
• 1301626-94-7 N-(3-(4-formylphenyl)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulfonamide 
• 1301627-03-1 N-(3-(furan-2-yl)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulfonamide 
• 1301627-04-2 N-(3-(furan-3-yl)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulfonamide 
• 850189-76-3 N-(3'-chloro-1',4'-dioxo-1',4'-dihydronaphthalen-2'-yl)benzenesulphonamide 

Relevant articles and documents

New aryloxy-quinone derivatives with promising activity on Trypanosoma cruzi

Continuing with a program to develop new quinone derivatives as biologically active compounds, we designed and synthesized a new series of aryloxy-quinones, which were evaluated in vitro against Trypanosoma cruzi in epimastigote form. Chemical modificatio

Discovery of Novel 2-Aniline-1,4-naphthoquinones as Potential New Drug Treatment for Leber's Hereditary Optic Neuropathy (LHON)

Leber's hereditary optic neuropathy (LHON) is a rare genetic mitochondrial disease and the primary cause of chronic visual impairment for at least 1 in 10 ?000 individuals in the U.K. Treatment options remain limited, with only a few drug candidates and therapeutic approaches, either approved or in development. Recently, idebenone has been investigated as drug therapy in the treatment of LHON, although evidence for the efficacy of idebenone is limited in the literature. NAD(P)H:quinone oxidoreductase 1 (NQO1) and mitochondrial complex III were identified as the major enzymes involved in idebenone activity. Based on this mode of action, computer-aided techniques and structure-activity relationship (SAR) optimization studies led to the discovery of a series naphthoquinone-related small molecules, with comparable adenosine 5′-triphosphate (ATP) rescue activity to idebenone. Among these, three compounds showed activity in the nanomolar range and one, 2-((4-fluoro-3-(trifluoromethyl)phenyl)amino)-3-(methylthio)naphthalene-1,3-dione (1), demonstrated significantly higher potency ex vivo, and significantly lower cytotoxicity, than idebenone.

Micelles catalyzed chemoselective synthesis 'in water' and biological evaluation of oxygen containing hetero-1,4-naphthoquinones as potential antifungal agents

Various oxygen containing 1,4-naphthoquinone derivatives have been synthesized chemoselectively by an economical, viable green methodology approach using water as solvent with or without surfactants such as Triton X-100, SDS, LD (laundry detergent), and T