Anthraquinone

9,10-Anthraquinone[1]
Names
Preferred IUPAC name
Anthracene-9,10-dione[2]
Other names
  • Anthraquinone
  • 9,10-Anthracenedione
  • Anthradione
  • 9,10-Anthrachinon
  • Anthracene-9,10-quinone
  • 9,10-Dihydro-9,10-dioxoanthracene
  • Hoelite
  • Morkit
  • Corbit
Identifiers
3D model (JSmol)
390030
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.408 Edit this at Wikidata
102870
KEGG
RTECS number
  • CB4725000
UNII
UN number 3143
  • 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
  • O=C1c2ccccc2C(=O)c3ccccc13
Properties
C14H8O2
Molar mass 208.216 g·mol−1
Appearance Yellow solid
Density 1.438 g/cm3[1]
Melting point 284.8 °C (544.6 °F; 558.0 K)[1]
Boiling point 377 °C (711 °F; 650 K)[1]
Insoluble
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 possible carcinogen
GHS labelling:
GHS08: Health hazard
Danger
H350
P201, P202, P281, P308+P313, 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).
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Anthraquinone, also called anthracenedione or dioxoanthracene, is an aromatic organic compound with formula C
14H
8O
2. Several isomers exist but these terms usually refer to 9,10-anthraquinone (IUPAC: 9,10-dioxoanthracene) wherein the keto groups are located on the central ring. It is used as a digester additive to wood pulp for papermaking. Many anthraquinone derivatives are generated by organisms or synthesised industrially for use as dyes, pharmaceuticals, and catalysts. Anthraquinone is a yellow, highly crystalline solid, poorly soluble in water but soluble in hot organic solvents. It is almost completely insoluble in ethanol near room temperature but 2.25 g will dissolve in 100 g of boiling ethanol. It is found in nature as the rare mineral hoelite.

  1. ^ a b c d Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. p. 3.28. ISBN 9781498754293.
  2. ^ International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 724. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.