6655-90-9

Basic information

• Product Name: 4-Chloro-1,2-naphthalenedione
• Synonyms: 4-Chloro-1,2-naphthalenedione;4-CHLORO-[1,2]NAPHTHOQUINONE;4-chloronaphthalene-1,2-dione;AURORA KA-5009;RARECHEM BW GA 0351;Zinc02552024
• CAS NO: 6655-90-9
• Molecular Formula: C₁₀H₅ClO₂
• Molecular Weight: 192.6
• Mol File: 6655-90-9.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 320.1 °C at 760 mmHg
• Flash Point: 134.7 °C
• Appearance: /
• Density: 1.42 g/cm³
• Vapor Pressure: 0.000326mmHg at 25°C
• Refractive Index: 1.625
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4-Chloro-1,2-naphthalenedione(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chloro-1,2-naphthalenedione(6655-90-9)
• EPA Substance Registry System: 4-Chloro-1,2-naphthalenedione(6655-90-9)

Safety Data

• Hazardous Substances Data: 6655-90-9(Hazardous Substances Data)

Usage

General Description

4-Chloro-1,2-naphthalenedione, also known as chlornaphazone, is a chemical compound used in the manufacturing of pharmaceutical drugs. It is a yellow crystalline powder that is insoluble in water but soluble in organic solvents. Chlornaphazone is a naphthoquinone derivative with anti-inflammatory and analgesic properties, and it has been used as an active ingredient in over-the-counter pain relief medications. It functions by inhibiting the synthesis of prostaglandins, which are involved in the body's inflammatory response and pain sensation. Additionally, chlornaphazone has been studied for its potential anti-cancer properties and its ability to modulate the immune system. Overall, 4-Chloro-1,2-naphthalenedione is a versatile compound with a variety of potential therapeutic applications.

InChI:InChI=1/C10H5ClO2/c11-8-5-9(12)10(13)7-4-2-1-3-6(7)8/h1-5H

Upstream product

• 604-44-4 4-chloronaphthalen-1-ol 
• 2050-76-2 2,4-dichloronaphthol 
• 75917-07-6 1,4-dichloro-[2]naphthol 
• 90-13-1 1-Chloronaphthalene 

Downstream Products

• 25282-86-4 2,3-dimethyl-phenanthrene-9,10-dione 
• 113092-58-3 4-nitro-benzoic acid-(4-chloro-1-hydroxy-[2]naphthyl ester) 
• 135467-69-5 4-phenoxynaphthalene-1,2-dione 
• 123433-19-2 4-(4-oxo-2-buten-1-ylidene)-2-hydroxynaphthalen-1(4H)-one 
• 123433-15-8 4-chloro-3',4'-dihydro-5'-methylspiro-1,4'-dione 
• 123433-18-1 4-chloro-3',6'-dihydro-4'-methoxyspiro-1,6'-dione 
• 123433-17-0 4-chloro-3',6'-dihydro-4'-methylspiro-1,6'-dione 
• 25107-86-2 4-[p-(1,1,3,3-Tetramethylbutyl)phenoxy]-1,2-naphthoquinone 
• 1785-67-7 1,2,4-triacetyloxynaphthalene 
• 959701-69-0 tert-butyl 4-{[(3,4-dioxo-3,4-dihydronaphthalen-1-yl)thio]methyl}-4-hydroxypiperidine-1-carboxylate 
• 112441-65-3 5-phenoxy-benzo[a]phenazine 
• 102001-85-4 1,2-diacetoxy-4-phenoxy-naphthalene 
• 959701-71-4 spiro[naphtho[1,2-b][1,4]oxathiine-2,4'-piperidine]-5,6-dione 

Relevant articles and documents

IBS-catalyzed regioselective oxidation of phenols to 1,2-quinones with oxone

We have developed the first example of hypervalent iodine(V)-catalyzed regioselective oxidation of phenols to o-quinones. Various phenols could be oxidized to the corresponding o-quinones in good to excellent yields using catalytic amounts of sodium salts of 2-iodobenzenesulfonic acids (pre-IBSes) and stoichiometric amounts of Oxone as a co-oxidant under mild conditions. The reaction rate of IBS-catalyzed oxidation under nonaqueous conditions was further accelerated in the presence of an inorganic base such as potassium carbonate (K2CO3), a phase transfer catalyst such as tetrabutylammonium hydrogen sulfate (nBu4NHSO4), and a dehydrating agent such as anhydrous sodium sulfate (Na2SO4).

Reactions of polar dienes with o-quinones

The behaviour of various types of polar dienes towards halogenated ortho quinones has been investigated in a number of representative cases.As compared to the commonly used para analogues, o-quinones provide a wide range of products that indicate a keener response to the nature, number, and position of substituents on both reactants. 3-Halogenated-o-naphthoquinones 1 and 2 react smoothly with a representative vinologous ketene acetal 3, vinylketene acetals 4 and 5, and a monooxygenated diene 6 to provide variously substituted phenanthrenequinones 7-11.Only monooxygenated dienes on the other hand add to o-benzoquinones 14-16 and give convenient syntheses of the corresponding o-naphthoquinones 18-20.Key words: cycloaddition, o-naphthoquinones, phenanthrenequinones, regiospecificity.