Naphthazarin

Naphthazarin
	Skeletal formula
	Ball-and-stick model
Names
	Preferred IUPAC name 5,8-Dihydroxynaphthalene-1,4-dione
	Other names Dihydroxynaphthoquinone
Identifiers
CAS Number	475-38-7 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEBI	CHEBI:28849 ;
ChEMBL	ChEMBL274056 ;
ChemSpider	9735 ;
ECHA InfoCard	100.006.816
EC Number	207-495-4;
KEGG	C01938;
PubChem CID	10141;
UNII	S9IX5I5C0K;
CompTox Dashboard (EPA)	DTXSID00197161 ;
	InChI InChI=1S/C10H6O4/c11-5-1-2-6(12)10-8(14)4-3-7(13)9(5)10/h1-4,11-12H Key: RQNVIKXOOKXAJQ-UHFFFAOYSA-N ; InChI=1/C10H6O4/c11-5-1-2-6(12)10-8(14)4-3-7(13)9(5)10/h1-4,11-12H Key: RQNVIKXOOKXAJQ-UHFFFAOYAN;
	SMILES C1=CC(=C2C(=O)C=CC(=O)C2=C1O)O; O=C\2c1c(O)ccc(O)c1C(=O)/C=C/2;
Properties
Chemical formula	C10H6O4
Molar mass	190.154 g·mol−1
Melting point	228–232 °C (442–450 °F; 501–505 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H312, H315, H319, H332, H335
Precautionary statements	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). verify (what is ?) 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
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.

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

Synthesis