Chemistry:Naphthazarin
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| Names | |
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| Preferred IUPAC name
5,8-Dihydroxynaphthalene-1,4-dione | |
| Other names
Dihydroxynaphthoquinone
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| Properties | |
| C10H6O4 | |
| Molar mass | 190.154 g·mol−1 |
| Melting point | 228–232 °C (442–450 °F; 501–505 K) |
| Hazards | |
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| GHS Signal word | Warning |
| H302, H312, H315, H319, H332, H335 | |
| P261, P264, P270, P271, P280, P301+312, P302+352, P304+312, P304+340, P305+351+338, P312, P321, P322, P330, P332+313, P337+313, P362, P363, P403+233, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
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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 C10H6O4, 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
- ↑ Thomson R.H. Naturally Occurring Quinones. Academic Press, London (1971). Quoted by Khalafy and Bruce.
- ↑ Thomson R.H. Naturally Occurring Quinones III. Chapman and Hall, London (1987). Quoted by Khalafy and Bruce.
- ↑ 3.0 3.1 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.
- ↑ Lewis J.R. and Paul J.J.(1977). Z. Naturforsch., B, 32: 1473. Quoted by Khalafy and Bruce.
- ↑ Huot R. and Brassard P. (1974). Can. J. Chem., 52: 838. Quoted by Khalafy and Bruce.
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