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Pigment violet 23

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Pigment violet 23
Names
Other names 9,19-Dichloro-5,15-diethyl-5,15-dihydrodiindolotriphenodioxazine, C.I. 51319, Carbazole Dioxazine Violet
Identifiers
CAS Number
3D model (JSmol)
ECHA InfoCard 100.108.962 Edit this at Wikidata
EC Number
  • 606-790-9
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C34H22Cl2N4O2/c1-3-39-19-11-7-5-9-17(19)25-21(39)13-15-23-29(25)37-31-27(35)34-32(28(36)33(31)41-23)38-30-24(42-34)16-14-22-26(30)18-10-6-8-12-20(18)40(22)4-2/h5-16H,3-4H2,1-2H3Key: GBNIRCSJWYOIHL-UHFFFAOYSA-N
SMILES
  • c1cc2N(CC)c3ccc4N=c5c(Cl)c6Oc7c8c9ccccc9N(CC)c8ccc7N=c6c(Cl)c5Oc4c3c2cc1
Properties
Chemical formula C34H22Cl2N4O2
Molar mass 589.48
Appearance dark purple solid
Melting point 385 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Pigment violet 23 is an organic compound that is a commercial pigment. It is member of the dioxazine family of heterocyclic compounds, but derived from carbazoles. It is prepared by condensation of chloranil and 3-amino-N-ethylcarbazole. It has a centrosymmetric angular structure. For many years, the structure was assigned, incorrectly, as having a "linear structure" (EC no. 228-767-9, CAS RN 6358-30-1) which differ in terms of the carbazole ring fusion.

Pigment violet 23 is prepared by condensation of an aniline with chloranil.

Synthetic route to dioxazine dyes such as pigment violet 23.

References

  1. Chamberlain, Terence "Dioxazine violet pigments" from High Performance Pigments Edited by Smith, Hugh M. 2002, 185–194. doi:10.1002/3527600493.ch12
  2. Panina, N.; van de Ven, R.; Verwer, P.; Meekes, H.; Vlieg, E.; Deroover, G. "Polymorph prediction of organic pigments" Dyes and Pigments 2008, volume 79, 183–192.
  3. Heinrich Zollinger (2003). Color Chemistry Syntheses, Properties, and Applications of Organic Dyes and Pigments. John Wiley & Sons. p. 118. ISBN 3-906390-23-3.
  4. Horst Tappe, Walter Helmling, Peter Mischke, Karl Rebsamen, Uwe Reiher, Werner Russ, Ludwig Schläfer and Petra Vermehren "Reactive Dyes"in Ullmann's Encyclopedia of Industrial Chemistry 2000, Wiley-VCH, Weinheim. doi:10.1002/14356007.a22_651
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