Bally-Scholl synthesis
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| Names | |
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IUPAC name
Anthraquinone
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| Other names
9,10-anthracenedione, anthradione, 9,10-anthrachinon, anthracene-9,10-quinone, 9,10-dihydro-9,10-dioxoanthracene, Hoelite, Morkit, Corbit
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| Identifiers | |
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3D model (JSmol)
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.001.408 |
| KEGG | |
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| Properties | |
| 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) |
| insoluble | |
| Hazards | |
| R-phrases (outdated) | R36/37/38 |
| Flash point | 185 °C (365 °F; 458 K) |
| Related compounds | |
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Related compounds
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quinone, anthracene |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 (what is   ?) |
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| 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: 9,10-dioxoanthracene) 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.
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