21890-57-3

Basic information

• Product Name: 3-chloro-5-hydroxy-2-methylnaphthalene-1,4-dione
• CAS NO: 21890-57-3
• Molecular Formula: C₁₁H₇ClO₃
• Molecular Weight: 222.6245
• Mol File: 21890-57-3.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 389.3°C at 760 mmHg
• Flash Point: 189.3°C
• Density: 1.49g/cm³
• Vapor Pressure: 1.28E-06mmHg at 25°C
• Refractive Index: 1.643
• CAS DataBase Reference: 3-chloro-5-hydroxy-2-methylnaphthalene-1,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 3-chloro-5-hydroxy-2-methylnaphthalene-1,4-dione(21890-57-3)
• EPA Substance Registry System: 3-chloro-5-hydroxy-2-methylnaphthalene-1,4-dione(21890-57-3)

Safety Data

• Hazardous Substances Data: 21890-57-3(Hazardous Substances Data)

Usage

General Description

3-chloro-5-hydroxy-2-methylnaphthalene-1,4-dione is an organic compound that belongs to the class of naphthoquinones. It is a derivative of naphthoquinone with a chloro and hydroxy group attached to the 3rd and 5th carbon atoms, respectively, and a methyl group attached to the 2nd carbon atom. This chemical compound has been studied for its potential use as an anti-inflammatory and anti-tumor agent due to its ability to inhibit the activity of certain enzymes and proteins involved in these processes. It has also been investigated for its potential use in the treatment of certain types of cancer due to its ability to induce cell death in cancer cells. Additionally, 3-chloro-5-hydroxy-2-methylnaphthalene-1,4-dione has been studied for its antioxidant properties and its potential use as a coloring agent in the food industry.

Synthetic route

5-hydroxy-2-methyl-1,4-naphthoquinone (481-42-5) → 5-hydroxy-2-methyl-3-chloro-1,4-naphthoquinone (21890-57-3) + 3,6-dichloro-5-hydroxy-2-methyl-[1,4]naphthoquinone (57093-07-9)

Conditions	Yield
With chlorine; acetic acid

5-hydroxy-2-methyl-1,4-naphthoquinone (481-42-5) → 5-hydroxy-2-methyl-3-chloro-1,4-naphthoquinone (21890-57-3)

Conditions	Yield
With chlorine In chloroform for 24h; Ambient temperature;	85 mg
With hydrogenchloride; potassium permanganate; acetic acid; sodium acetate for 1h;	240 mg

3-Chlorplumbaginacetat (76855-75-9) → 5-hydroxy-2-methyl-3-chloro-1,4-naphthoquinone (21890-57-3)

Conditions	Yield
With aluminium trichloride In dichloromethane for 3h; Ambient temperature;

3-chlorojuglone (18855-92-0) + dimethyl sulfoxide (67-68-5) → 5-hydroxy-2-methyl-3-chloro-1,4-naphthoquinone (21890-57-3)

Conditions	Yield
With dihydrogen peroxide 1.) dioxan, room temp., 30 min, 2.) dioxan, 15 min; Yield given. Multistep reaction;

5-Acetoxy-3-chlor-1,4-naphthochinon (91855-98-0) + dimethyl sulfoxide (67-68-5) → 5-hydroxy-2-methyl-3-chloro-1,4-naphthoquinone (21890-57-3)

Conditions	Yield
Yield given. Multistep reaction;

5-Acetoxy-3-chlor-1,4-naphthochinon (91855-98-0) → 5-hydroxy-2-methyl-3-chloro-1,4-naphthoquinone (21890-57-3) + 3-Chlor-5-hydroxy-2-(4-nitrophenyl)-1,4-naphthochinon

Conditions	Yield
With ammonium peroxydisulfate; aluminium trichloride; silver nitrate; 4-nitro-benzoic acid 1.) CH3CN, water, 80 deg C, 40 min, 2.) CH2Cl2, r.t., 3 h; Yield given. Multistep reaction. Yields of byproduct given;

5-Acetoxy-3-chlor-1,4-naphthochinon (91855-98-0) + 4-nitro-benzoic acid (62-23-7) → 5-hydroxy-2-methyl-3-chloro-1,4-naphthoquinone (21890-57-3) + nitrobenzene (98-95-3) + 3-Chlor-5-hydroxy-2-(4-nitrophenyl)-1,4-naphthochinon

Conditions	Yield
With ammonium peroxydisulfate; aluminium trichloride; silver nitrate 1.) CH3CN, water, 80 deg C, 40 min, 2.) CH2Cl2, r.t., 3 h; Yield given. Multistep reaction. Yields of byproduct given;

5-hydroxy-2-methyl-1,4-naphthoquinone (481-42-5) → 5-hydroxy-2-methyl-3-chloro-1,4-naphthoquinone (21890-57-3) + 2-methyl-5-hydroxy-2,3-epoxy-2,3-dihydro-1,4-naphthoquinone (188675-38-9)

Conditions	Yield
With hydrogenchloride; sodium perborate; sulfuric acid 1.) ethanol, 2 min; Yield given. Multistep reaction. Yields of byproduct given;

acetic acid (64-19-7) + 3-chloro-5-hydroxy-naphthoquinone-(1.4) → 5-hydroxy-2-methyl-3-chloro-1,4-naphthoquinone (21890-57-3)

Conditions	Yield
With diacetyl peroxide

5-hydroxy-2-methyl-1,4-naphthoquinone (481-42-5) → 5-hydroxy-2-methyl-3-chloro-1,4-naphthoquinone (21890-57-3) + 3,6(?)-dichloro-5-hydroxy-2-methyl-<1,4>naphthoquinone

Conditions	Yield
With chlorine; acetic acid

5-Acetoxy-3-chlor-1,4-naphthochinon (91855-98-0) → 5-hydroxy-2-methyl-3-chloro-1,4-naphthoquinone (21890-57-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 0 - 5 °C 2: AlCl3 / CH2Cl2 / 3 h / Ambient temperature View Scheme

5-hydroxy-2-methyl-3-chloro-1,4-naphthoquinone (21890-57-3) → 3-chloro-6-nitroplumbagin + 3-chloro-8-nitroplumbagin

Conditions	Yield
With sulfuric acid; nitric acid for 1h; Ambient temperature;	A 37% B 49%

methanol (67-56-1) + 5-hydroxy-2-methyl-3-chloro-1,4-naphthoquinone (21890-57-3) → 5-Hydroxy-3-methoxy-2-methyl-1,4-naphthochinon (61836-29-1)

Conditions	Yield
With sodium hydroxide for 2h; Ambient temperature;	10%

5-hydroxy-2-methyl-3-chloro-1,4-naphthoquinone (21890-57-3) + ethanethiol (75-08-1) → 3-ethylsulfanyl-5-hydroxy-2-methyl-[1,4]naphthoquinone

Conditions	Yield
With pyridine; ethanol

Upstream product

• 91855-98-0 5-Acetoxy-3-chlor-1,4-naphthochinon 
• 481-42-5 5-hydroxy-2-methyl-1,4-naphthoquinone 
• 64-19-7 acetic acid 
• 62-23-7 4-nitro-benzoic acid 
• 67-68-5 dimethyl sulfoxide 
• 18855-92-0 3-chlorojuglone 
• 76855-75-9 3-Chlorplumbaginacetat 

Relevant articles and documents

1,4-Naphthoquinones, xx: Droserone, ethers and isomers from juglone

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NAPHTHOQUINONES FROM DIONAEA MUSCIPULA

Beside the known naphthoquinone, plumbagin, the new compound hydroplumbagin 4-O-β-glucopyranoside has been isolated from a methanolic extract of Dionaea muscipula, together with two known naphthoquinones, droserone and 3-chloroplumbagin which have not been reported previously from this plant.Structure determination of hydroplumbagin 4-O-glucoside was carried out unambiguously by NOE experiments.

Synthesis of some plumbagin derivatives and their antibacterial activity

Several plumbagin derivatives were synthesized from plumbagin and tested for their antimicrobial activity.

Method for dyeing keratinous fibres using a monohydroxyindole or dihydroxyindole and a non-oxidizing aromatic carbonyl derivative and dyeing agent

The present invention relates to a method for dyeing keratinous fibers, characterized in that the following are applied to the fibers: a) a composition (A) containing, in a medium appropriate for dyeing, at least one monohydroxyindole or dihydroxyindole, this application being preceded or followed by the application of b) a composition (B) containing, in a medium appropriate for dyeing, at least one aromatic carbonyl derivative chosen from hydroxyacetophenones, hydroxybenzophenones, 2-hydroxy-1,4-benzoquinones, hydroxy-1,4-naphthoquinones,amino-1,4-naphthoquinones,hydroxy-9,10-anthraquinones and amino-9,10-anthraquinones. It also relates to the dyeing agents for carrying it out.