Anthraquinone

Anthraquinone, also called anthracenedione or dioxoanthracene, is an aromatic organic compound with formula C
14
H
8
O
2
. Isomers include various quinone derivatives. The term anthraquinone however refers to the 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. 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.

9,10-Anthraquinone
Names
Preferred IUPAC name
Anthracene-9,10-dione
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
102870
KEGG
PubChem CID
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
SMILES
  • O=C1c2ccccc2C(=O)c3ccccc13
Properties
C14H8O2
Molar mass 208.216 g·mol−1
Appearance Yellow solid
Density 1.438 g/cm3
Melting point 284.8 °C (544.6 °F; 558.0 K)
Boiling point 377 °C (711 °F; 650 K)
Insoluble
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
possible carcinogen
GHS labelling:
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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Infobox references
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