5,8-Dihydroxy-1,4-naphthoquinone

5,8-Dihydroxy-1,4-naphthoquinone
Names
IUPAC name
5,8-dihydroxynaphthalene-1,4-dione
Other names
Dihydroxynaphthoquinone
Identifiers
ChEBI CHEBI:28849 N
ChEMBL ChEMBL274056 YesY
ChemSpider 9735 YesY
Jmol interactive 3D Image
Image
PubChem 10141
Properties
C10H6O4
Molar mass 190.15 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Naphthazarin, often called 5,8-dihydroxy-1,4-naphthoquinone or 5,8-dihydroxy-1,4-naphthalenedione (IUPAC), is a naturally occurring[1][2] organic compound with formula C
10
H
6
O
4
, formally derived from 1,4-naphthoquinone through replacement of two hydrogen atoms by hydroxyl (OH) groups. It is thus one of many dihydroxynaphthoquinone structural isomers.

Naphthazarin is soluble in 1,4-dioxane from which it crystallizes as deep red needles that melt at 228−232 °C.[3]

Synthesis

Naphtharazin can be prepared by condensation of 1,4-dimethoxybenzene with 2,3-dichloromaleic anhydride followed by reductive dechlorination and reoxidation.[4][5]

Naphtharazin can also be obtained by oxidation of 5,8-dihydroxy-1-tetralone with manganese dioxide (MnO2).[3]

References

  1. Thomson R.H. Naturally Occurring Quinones. Academic Press, London (1971). Quoted by Khalafy and Bruce.
  2. Thomson R.H. Naturally Occurring Quinones III. Chapman and Hall, London (1987). Quoted by Khalafy and Bruce.
  3. 1 2 J. Khalafy and J.M. Bruce (2002), Oxidative dehydrogenation of 1-tetralones: Synthesis of juglone, naphthazarin, and α-hydroxyanthraquinones. Journal of Sciences, Islamic Republic of Iran, volume 13 issue 2, pages 131-139.
  4. Lewis J.R. and Paul J.J.(1977). Z. Naturforsch., B, 32: 1473. Quoted by Khalafy and Bruce.
  5. Huot R. and Brassard P. (1974). Can. J. Chem., 52: 838. Quoted by Khalafy and Bruce.
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