1,4-Dihydroxyanthraquinone

1,4-Dihydroxyanthraquinone
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name
1,4-Dihydroxyanthracene-9,10-dione
Other names
Quinizarin; Solvent Orange 86
Identifiers
CAS Number
  • 81-64-1 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:37487 checkY
ChEMBL
  • ChEMBL17594 checkY
ChemSpider
  • 6433 checkY
ECHA InfoCard 100.001.245 Edit this at Wikidata
PubChem CID
  • 6688
UNII
  • 8S496ZV3CS checkY
CompTox Dashboard (EPA)
  • DTXSID8044464 Edit this at Wikidata
InChI
  • InChI=1S/C14H8O4/c15-9-5-6-10(16)12-11(9)13(17)7-3-1-2-4-8(7)14(12)18/h1-6,15-16H checkY
    Key: GUEIZVNYDFNHJU-UHFFFAOYSA-N checkY
  • InChI=1/C14H8O4/c15-9-5-6-10(16)12-11(9)13(17)7-3-1-2-4-8(7)14(12)18/h1-6,15-16H
    Key: GUEIZVNYDFNHJU-UHFFFAOYAX
  • O=C2c1ccccc1C(=O)c3c2c(O)ccc3O
Properties
Chemical formula
 C14H8O4
Molar mass 240.21 g/mol
Appearance Orange or red-brown crystalline powder
Melting point 198 to 199 °C (388 to 390 °F; 471 to 472 K)
Boiling point 450 °C (842 °F; 723 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references
Chemical compound

1,4-Dihydroxyanthraquinone, also called quinizarin or Solvent Orange 86, is an organic compound derived from anthroquinone. Quinizarin is an orange or red-brown crystalline powder. It is formally derived from anthraquinone by replacement of two hydrogen atoms by hydroxyl (OH) groups. It is one of ten dihydroxyanthraquinone isomers and occurs in small amounts (as a glycoside) in the root of the madder plant, Rubia tinctorum.[1]

Production

Quinizarin is produced by the reaction of phthalic anhydride and 4-chlorophenol followed by hydrolysis of the chloride:[2][3]

Summary equation for one synthesis of alizarin.

It can also be prepared less efficiently from phthalic anhydride and hydroquinone.

Uses

Quinizarin is an inexpensive dye that is used to colour gasoline and some heating oils. It is used as an intermediate for the synthesis of indanthrene- and alizarin-derived dyes. The OH groups can be replaced by chloride. Chlorination and bromination afford other dyes. Amination (replacement of one OH by ArNH) with aniline derivatives followed by sulfonation affords other dyes such as Acid Violet 43. It is also used to form lake pigments with calcium, barium, and lead.[2]

Quinizarin sample (Historic Dye Collection of TU Dresden).

See also

References

  1. ^ Derksen, G. C. H.; Niederländer, H. A. G.; van Beek, T. A. (2002). "Analysis of Anthraquinones in Rubia tinctorum L. by Liquid Chromatography Coupled with Diode-Array UV and Mass Spectrometric Detection". Journal of Chromatography A. 978 (1–2): 119–127. doi:10.1016/S0021-9673(02)01412-7. PMID 12458949.
  2. ^ a b Bien, H.-S.; Stawitz, J.; Wunderlich, K. "Anthraquinone Dyes and Intermediates". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_355. ISBN 978-3527306732.
  3. ^ Bigelow, L. A.; Reynolds, H. H. (1926). "Quinizarin". Org. Synth. 6: 78. doi:10.15227/orgsyn.006.0078.