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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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Identifiers | |
3D model (
JSmol)
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ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.006.816 |
EC Number |
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KEGG | |
PubChem
CID
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UNII | |
CompTox Dashboard (
EPA)
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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 | |
GHS labelling: | |
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Warning | |
H302, H312, H315, H319, H332, H335 | |
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, 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 C
10H
6O
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]
Naphtharazin can be prepared by condensation of 1,4-dimethoxybenzene with 2,3-dichloromaleic anhydride followed by reductive dechlorination and re oxidation. [4] [5]
Naphtharazin can also be obtained by oxidation of 5,8-dihydroxy-1-tetralone with manganese dioxide (MnO2). [3]