Pigment violet 23

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

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
CAS Number	215247-95-3
3D model (JSmol)	Interactive image
ECHA InfoCard	100.108.962
EC Number	606-790-9
PubChem CID	20813033
CompTox Dashboard (EPA)	DTXSID2036293
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,3-4H2,1-2H3 Key: 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 [77 °F], 100 kPa). Infobox references

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

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