Anthraquinone

Title: Anthraquinone
CAS Registry Number: 84-65-1
CAS Name: 9,10-Anthracenedione
Additional Names: 9,10-anthraquinone; 9,10-dioxoanthracene
Trademarks: Flight Control (DCV)
Molecular Formula: C14H8O2
Molecular Weight: 208.21
Percent Composition: C 80.76%, H 3.87%, O 15.37%
Literature References: Prepn: A. Laurent, Ann. 34, 287 (1840). Structural relationship with anthracene: C. Graebe, C. Liebermann, Ber. 2, 332 (1869). Industrial prepn from phthalic anydride and benzene: Klipstein, Ind. Eng. Chem. 18, 1327 (1926). From anthracene with vanadium pentoxide, sodium chlorate, glacial acetic and sulfuric acids: Org. Synth. coll. vol. II, 554 (1943). Convenient lab procedure: L. F. Fieser, Organic Experiments (Heath & Co., Boston, 1964) pp 195-200. Review of chemistry: M. Phillips, Chem. Rev. 6, 157 (1929); of manufacture and uses: A. J. Cofrancesco in Kirk-Othmer Encyclopedia of Chemical Technology Vol. 2 (Wiley-Interscience, New York, 4th ed., 1992) pp 801-814. Development as bird repellent: R. M. Poché, Proc. 18th Vertebr. Pest Conf. 1998, 338. Field trial to control Canadian geese: P. Devers et al. ibid. 345.
Properties: Light yellow, slender monoclinic prisms by sublimation in vacuo. Almost colorless, orthorhombic, bipyramidal crystals from H2SO4 + H2O. d420 1.42-1.44. mp 286°. bp760 377°. Absorption spectrum: Flexser et al., J. Am. Chem. Soc. 57, 2103 (1935). Insol in water. Solubility (g/100 g) in alc at 18° 0.05; at 25° 0.44; in boiling alc 2.25; in ether at 25° 0.11; in chloroform at 20° 0.61; at 40° 1.00; at 60° 1.60; in benzene at 20° 0.26; at 40° 0.50; at 60° 1.00; at 80° 1.80; in toluene at 25° 0.30.
Melting point: mp 286°
Boiling point: bp760 377°
Density: d420 1.42-1.44
CAUTION: Low acute oral toxicity, but may cause skin irritation, sensitization. See Clinical Toxicology of Commercial Products, R. E. Gosselin et al., Eds. (Williams & Wilkins, Baltimore, 5th ed., 1984) Section II, p 189.
Use: Starting material for the manufacture of dyes; bird repellent.
Anthrarobin Anthrarufin Anthrimide Anthrone Antimony Chloride Oxide

9,10-Anthraquinone
Skeletal formula
Ball-and-stick model
Identifiers
CAS number 84-65-1 YesY
ChemSpider 6522 YesY
KEGG C16207 YesY
ChEBI CHEBI:40448 N
ChEMBL CHEMBL55659 N
Jmol-3D images Image 1
Properties
Molecular formula C14H8O2
Molar mass 208.21 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
Hazards
R-phrases R36/37/38
Flash point 185 °C; 365 °F; 458 K
Related compounds
Related compounds quinone,
anthracene
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Anthraquinone, also called anthracenedione or dioxoanthracene, is an aromatic organic compound with formula C
14
H
8
O
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.