21890-57-3

Usage

Uses

Used in Pharmaceutical Industry:
3-chloro-5-hydroxy-2-methylnaphthalene-1,4-dione is used as an anti-inflammatory and anti-tumor agent for its ability to inhibit the activity of certain enzymes and proteins involved in inflammation and tumor growth.
Used in Cancer Treatment:
3-chloro-5-hydroxy-2-methylnaphthalene-1,4-dione is used as a potential treatment for certain types of cancer due to its ability to induce cell death in cancer cells.
Used in Food Industry:
3-chloro-5-hydroxy-2-methylnaphthalene-1,4-dione is used as a potential coloring agent in the food industry, taking advantage of its antioxidant properties to enhance the stability and appearance of food products.

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

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

Relevant academic research and scientific papers

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.

Preparation of naphthoquinone derivatives from plumbagin and their ichthyotoxicity

Various naphthoquinone derivatives were prepared from a natural product, 5-hydroxy-2-methyl-1,4-naphthoquinone (plumbagin); these were mostly substituted at C-3 through carbon-carbon bond formation mediated by a metal- based oxidant such as lead tetraacetate in the presence of various carboxylic acids. The halogenated compounds showed stronger ichthyotoxicity than plumbagin, but other derivatives were less active.

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.

1,4-Naphthoquinones. XXIII: 2/3-Halogeno-2/3-nitrophenyl-juglone derivatives, synthesis and cytotoxic properties

Radical arylation of 1,4-naphthoquinones is possible by oxidative decarboxylation of 2- and 4-nitrobenzoic acid. With 2- and 3-halogenojuglone derivatives the 4-nitrophenyl compounds 10-13 are prepared in good, the 2-nitrophenyl analogues 14-17 only in poor yields. - All compounds are inactive against the virus types HSV and HIV and their marked cytotoxicity in part depends on the substitution pattern. The 3-aryl and o-nitro derivatives are more active than their 2-aryl and p-nitro analogues and the influence of the chloro or bromo substitution is only remarkable in the case of 12/13.

1,4-Naphthoquinones, VII: C-Methylation of 1,4-Naphthoquinones

The action of Fenton's reagent on dimethyl sulfoxide results in carbon methylation of the quinoid system of 1,4-naphthoquinones by .CH3 under particularly mild conditions.The results depend on the substitution pattern at positions 2 and 3 and on the suitable protection of the OH group at position 5.