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

Description

2-chloro-3-phenoxynaphthoquinone is a chemical compound belonging to the family of naphthoquinone derivatives. It is a chlorinated derivative of phenoxynaphthoquinone, characterized by a naphthoquinone core with a chlorine atom at position 2 and a phenoxy group at position 3. This unique chemical structure endows it with versatile reactivity and compatibility with various functional groups, making it a valuable compound in organic synthesis.

Uses

Used in Organic Synthesis:
2-chloro-3-phenoxynaphthoquinone is used as a reagent in organic synthesis for its ability to participate in electrophilic substitution and oxidative coupling reactions. Its unique structure allows for the creation of a wide range of chemical products.
Used in Dye Production:
In the dye industry, 2-chloro-3-phenoxynaphthoquinone is used as a key intermediate in the production of various dyes. Its chemical properties contribute to the development of dyes with specific color characteristics and stability.
Used in Pharmaceutical Development:
2-chloro-3-phenoxynaphthoquinone is utilized in the pharmaceutical industry for its potential biological activities and pharmacological properties. Its versatile reactivity and functional group compatibility make it a promising candidate for the development of new drugs.
Used in Agrochemicals:
In agrochemicals, 2-chloro-3-phenoxynaphthoquinone is used as a component in the synthesis of various agrochemical products. Its reactivity and functional group compatibility contribute to the development of effective and targeted agrochemicals.
Used in Medicinal Chemistry Research:
2-chloro-3-phenoxynaphthoquinone is also a valuable target for medicinal chemistry research. Its potential biological activities and pharmacological properties make it an interesting subject for the development of new therapeutic agents and the study of molecular interactions.

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

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