5350-26-5

Basic information

• Product Name: 2-dimethylamino-3-chloro-1,4-naphthoquinone
• Synonyms: 2-dimethylamino-3-chloro-1,4-naphthoquinone;2-Chloro-3-(dimethylamino)-1,4-naphthoquinone
• CAS NO: 5350-26-5
• Molecular Formula: C₁₂H₁₀ClNO₂
• Molecular Weight: 235.67
• Mol File: 5350-26-5.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 315.5°Cat760mmHg
• Flash Point: 144.6°C
• Appearance: /
• Density: 1.34g/cm³
• Vapor Pressure: 0.000436mmHg at 25°C
• Refractive Index: 1.613
• CAS DataBase Reference: 2-dimethylamino-3-chloro-1,4-naphthoquinone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-dimethylamino-3-chloro-1,4-naphthoquinone(5350-26-5)
• EPA Substance Registry System: 2-dimethylamino-3-chloro-1,4-naphthoquinone(5350-26-5)

Safety Data

• Hazardous Substances Data: 5350-26-5(Hazardous Substances Data)

Usage

General Description

2-dimethylamino-3-chloro-1,4-naphthoquinone is a chemical compound with the molecular formula C12H10ClNO2. It is a chlorinated naphthoquinone derivative, and its structure consists of a naphthalene ring system with a chlorine atom and a dimethylamino group attached to it. 2-dimethylamino-3-chloro-1,4-naphthoquinone is known for its redox properties and is often used as a redox indicator in analytical chemistry. It can undergo reversible oxidation and reduction, making it useful in determining the presence of certain analytes in chemical reactions. Additionally, it has been found to exhibit cytotoxic activity and may have potential applications in pharmaceutical research.

InChI:InChI=1/C12H10ClNO2/c1-14(2)10-9(13)11(15)7-5-3-4-6-8(7)12(10)16/h3-6H,1-2H3

Upstream product

• 2348-79-0 2-dimethylamino-1,4-naphthoquinone 
• 117-80-6 2,3-Dichloro-1,4-naphthoquinone 
• 86-21-5 pheniramine 
• 605-69-6 1-hydroxy-2,4-dinitronaphthalene 
• 303-69-5 prothipendyl 
• 124-40-3 dimethyl amine 

Downstream Products

• 1526-73-4 3-chloro-2-hydroxy-naphthalene-1,4-dione 
• 124-40-3 dimethyl amine 
• 134717-19-4 2-Dimethylamino-3-phenylselanyl-[1,4]naphthoquinone 

Relevant articles and documents

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.

Reactions of trialkylamine compounds with 2,3-dichloro-1,4-naphthoquinone

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