9,10-anthraquinone

9,10-Anthraquinone

Names
Preferred IUPAC name Anthracene-9,10-dione
Other names 9,10-Anthraquinone Anthraquinone 9,10-Anthracenedione Anthradione 9,10-Anthrachinon Anthracene-9,10-quinone 9,10-Dihydro-9,10-dioxoanthracene Hoelite Morkit Corbit
Identifiers
CAS Number	84-65-1 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:40448 N
ChemSpider	6522 Y
ECHA InfoCard	100.001.408
EC Number	201-549-0
KEGG	C16207 Y
PubChem CID	6780
UNII	030MS0JBDO
UN number	3143
InChI InChI=1S/C14H8O2/c15-13-9-5-1-2-6-10(9)14(16)12-8-4-3-7-11(12)13/h1-8H Key: RZVHIXYEVGDQDX-UHFFFAOYSA-N
SMILES O=C1c2ccccc2C(=O)c3ccccc13
Properties
Chemical formula	C14H8O2
Molar mass	208.22 g·mol−1
Appearance	yellow solid
Density	1.308 g/cm3
Melting point	286 °C (547 °F; 559 K)
Boiling point	379.8 °C (715.6 °F; 653.0 K)
Solubility in water	insoluble
Magnetic susceptibility (χ)	-119.6·10−6 cm3/mol
Hazards
GHS pictograms
GHS signal word	Warning
GHS hazard statements	H320, H351, H373, H400, H410
GHS precautionary statements	P201, P202, P260, P264, P273, P281, P305+351+338, P308+313, P314, P337+313, P391, P405, P501
Flash point	185 °C (365 °F; 458 K)
Related compounds
Related compounds	quinone, anthracene
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Anthraquinone, also called anthracenedione or dioxoanthracene, is an aromatic organic compound with formula C
14H
8O
2. Several isomers are possible, each of which can be viewed as a quinone derivative. The term anthraquinone, however, almost invariably refers to one specific isomer, 9,10-anthraquinone (IUPAC: anthracene-9,10-dione) wherein the keto groups are located on the central ring. It is a building block of many dyes and is used in bleaching pulp for papermaking. It is a yellow highly crystalline solid, poorly soluble in water but soluble in hot organic solvents. For instance, it is almost completely insoluble in ethanol near room temperature but 2.25 g will dissolve in 100 g of boiling ethanol.

9,10-Anthraquinone is obtained industrially by the oxidation of anthracene, a reaction that is localized at the central ring. Chromium(VI) is the typical oxidant. It is also prepared by the Friedel-Crafts reaction of benzene and phthalic anhydride in presence of AlCl₃. The resulting o-benzoylbenzoic acid then undergoes cyclization, forming anthraquinone. This reaction is useful for producing substituted anthraquinones. The Diels-Alder reaction of naphthoquinone and butadiene followed by oxidative dehydrogenation will also produce 9,10-anthraquinone. Lastly, BASF has developed a process that proceeds via the acid-catalyzed dimerization of styrene to give a 1,3-diphenylbutene, which then can be transformed to the anthaquinone. It also arises via the Rickert-Alder reaction, a retro-Diels-Alder reaction.