15254-76-9

Basic information

• Product Name: 8-Hydroxy-2-methoxy-1,4-naphthalenedione
• Synonyms: 8-Hydroxy-2-methoxy-1,4-naphthalenedione;8-Hydroxy-2-methoxy-1,4-naphthoquinone
• CAS NO: 15254-76-9
• Molecular Formula: C11H8O4
• Molecular Weight: 204.18
• Mol File: 15254-76-9.mol
• Article Data: 7

Chemical Properties

• Melting Point: 240 °C
• Boiling Point: 419.9±45.0 °C(Predicted)
• Appearance: /
• Density: 1.41±0.1 g/cm3(Predicted)
• PKA: 6.40±0.20(Predicted)
• CAS DataBase Reference: 8-Hydroxy-2-methoxy-1,4-naphthalenedione(CAS DataBase Reference)
• NIST Chemistry Reference: 8-Hydroxy-2-methoxy-1,4-naphthalenedione(15254-76-9)
• EPA Substance Registry System: 8-Hydroxy-2-methoxy-1,4-naphthalenedione(15254-76-9)

Safety Data

• Hazardous Substances Data: 15254-76-9(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 481-39-0 5-hydroxynaphtho-1,4-quinone 
• 18855-92-0 3-chlorojuglone 
• 52431-65-9 3-Bromojuglone 
• 4923-57-3 2-chlorojuglone 
• 69008-03-3 2-bromo-5-hydroxy-[1,4]naphthoquinone 
• 124-41-4 sodium methylate 
• 106697-17-0 2-Chloro-3-methoxyjuglone 
• 106697-18-1 2-Brom-5-hydroxy-3-methoxy-1,4-naphthochinon 
• 82961-14-6 3,4-dihydro-8-hydroxy-5,7-dimethoxy-1(2H)-naphthalenone 
• 31914-19-9 4-(2',4',5'-trimethoxyphenyl)-4-oxobutanoic acid 
• 3905-27-9 4-(2',4',5'-trimethoxyphenyl)butanoic acid 
• 4923-60-8 2,3-dichloro-5-hydroxy-1,4-naphthoquinone 
• 93831-47-1 2,3-Dibromo-2,3-dihydro-5-hydroxy-1,4-naphthoquinone 

Downstream Products

• 4923-58-4 3,5-dihydroxy-2,3-dihydro-1,4-naphthoquinone 
• 4923-55-1 2-Hydroxyjuglon 

Relevant articles and documents

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.

Regiospecific Addition of Monooxygenated Dienes to Halo Quinones

In spite of their decreased polarity with respect to previously studied electron-rich analogues, monooxygenated dienes also react regiospecifically with halo quinones.The corresponding adducts can easily be aromatized on silica gel to isomeric polysubstituted naphthoquinones of unambiguous structure and therefore provide ready access to substrates for subsequent regiospecific annulations.The scope of this approach is illustrated by advantageous syntheses of several natural products: chimaphilin, 6-methylalizarin, 6-methylxantopurpurin, and barleriaquinone.The adductscan also give rise to a series of products in which the oxygen function of the dienes is preserved as a hydroxyl group in the quinone.To this end adducts derived from 1-oxygenated dienes and halo quinones were oxidized effectively with Jones reagent while those obtained from the 2-oxygenated isomers responded better to manganese dioxide.Relative positions of substituens in the adducts were readily confirmed by comparison of some of the hydroxylated oxidation products with known compounds of unambiguous structure.The method is again illustrated by the ready synthesis of a number of natural products including plumbagin, soranjidiol, isochrysophanol and its 8-methyl ether, and isozyganein and its 5-methyl ether.