Pigment violet 23

Last updated
Pigment violet 23
C.I. Pigment Violet 23.svg
Names
Other names
9,19-Dichloro-5,15-diethyl-5,15-dihydrodiindolo[2,3-c:2',3'-n]triphenodioxazine, C.I. 51319, Carbazole Dioxazine Violet
Identifiers
3D model (JSmol)
ChemSpider
  • incorrect linear form: 55316
ECHA InfoCard 100.108.962 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 606-790-9
PubChem CID
  • 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,3-4H2,1-2H3
    Key: GBNIRCSJWYOIHL-UHFFFAOYSA-N
  • c1cc2N(CC)c3ccc4N=c5c(Cl)c6Oc7c8c9ccccc9N(CC)c8ccc7N=c6c(Cl)c5Oc4c3c2cc1
Properties
C34H22Cl2N4O2
Molar mass 589.48
Appearancedark purple solid
Melting point 385 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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. [1] It is prepared by condensation of chloranil and 3-amino-N-ethylcarbazole. It has a centrosymmetric angular structure. [2] 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. [3]

Pigment violet 23 is prepared by condensation of an aniline with chloranil. [4]

Synthetic route to dioxazine dyes such as pigment violet 23. DioxazineFrChloranil.png
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