Pigment Yellow 83

Pigment Yellow 83
Names
	Other names Enceprint Yellow 1780, Homapol Yellow PO-227
Identifiers
CAS Number	5567-15-7 ;
3D model (JSmol)	Interactive image;
ChemSpider	20428;
ECHA InfoCard	100.024.491
EC Number	226-939-8;
PubChem CID	21733;
UNII	67HO7X7FV3 ;
CompTox Dashboard (EPA)	DTXSID1021453 ;
	InChI InChI=1S/C36H32Cl4N6O8/c1-17(47)33(35(49)41-27-15-29(51-3)23(39)13-31(27)53-5)45-43-25-9-7-19(11-21(25)37)20-8-10-26(22(38)12-20)44-46-34(18(2)48)36(50)42-28-16-30(52-4)24(40)14-32(28)54-6/h7-16,33-34H,1-6H3,(H,41,49)(H,42,50)/b45-43+,46-44+ Key: NKXPXRNUMARIMZ-MWOVFPFUSA-N;
	SMILES COc1cc(Cl)c(OC)cc1NC(=O)C(C(=O)C)/N=Nc2ccc(cc2Cl)-c3cc(Cl)c(cc3)/N=N/C(C(=O)C)C(=O)Nc4cc(OC)c(Cl)cc4OC;
Properties
Chemical formula	C36H32Cl4N6O8
Molar mass	818.49 g·mol−1
Appearance	Yellow solid
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Color Index Pigment Yellow 83 is an organic compound that is classified as a diarylide pigment. It is used as a yellow colorant.

Production

The compound is produced industrially from three components: Treatment of 2,5-dimethoxy-4-chloroaniline with diketene gives an acetoacetylated aniline. This compound is then coupled to the bisdiazonium salt obtained from 3,3'-dichlorobenzidine.^[1]

Properties

Pigment Yellow 83 is a slightly flammable yellow solid that is practically insoluble in water. It decomposes when heated above 300 °C.^[2] It exhibits a crystal structure belonging to the space group P21/c or space group Pc.^[3]

As confirmed by X-ray crystallography, the compound exists as a bis(keto-hydrazide) tautomer, not a true diazo compound.^[4]

Use

Pigment Yellow 83 is used, for example, as a reddish-yellow pigment in printing inks and plastics.^[5]^[6]

References

^ K. Hunger. W. Herbst "Pigments, Organic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2012. doi:10.1002/14356007.a20_371
^ Record of Pigment Yellow 83 in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 2020-03-30.
^ Martin U. Schmidt, Robert E. Dinnebier, Holger Kalkhof: Crystal Engineering on Industrial Diaryl Pigments Using Lattice Energy Minimizations and X-ray Powder Diffraction. In: The Journal of Physical Chemistry B. 111, 2007, S. 9722, doi:10.1021/jp071731p.
^ Barrow, Michael J.; Christie, Robert M.; Badcock, Tracey D. (2003). "The crystal and molecular structure of C.I. Pigment Yellow 83, a superior performance Diarylide Yellow pigment". Dyes and Pigments. 57 (2): 99–106. doi:10.1016/S0143-7208(02)00117-1.
^ Werner Baumann, Thomas Rothardt (2013), [[1], p. 585, at Google Books Druckerei-chemikalien Daten und Fakten zum Umweltschutz 2., erweiterte und überarbeitete Auflage], Springer-Verlag, p. 585, ISBN 978-3-642-58474-9 {{citation}}: Check |url= value (help)
^ Willy Herbst, Klaus Hunger (2009), [[2], p. 261, at Google Books Industrielle Organische Pigmente Herstellung, Eigenschaften, Anwendung], John Wiley & Sons, p. 261, ISBN 3-527-62496-1 {{citation}}: Check |url= value (help)

[Ullmann1-1] K. Hunger. W. Herbst "Pigments, Organic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2012. doi:10.1002/14356007.a20_371

[GESTIS-2] Record of Pigment Yellow 83 in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 2020-03-30.

[DOI10.1021/jp071731p-3] Martin U. Schmidt, Robert E. Dinnebier, Holger Kalkhof: Crystal Engineering on Industrial Diaryl Pigments Using Lattice Energy Minimizations and X-ray Powder Diffraction. In: The Journal of Physical Chemistry B. 111, 2007, S. 9722, doi:10.1021/jp071731p.

[4] Barrow, Michael J.; Christie, Robert M.; Badcock, Tracey D. (2003). "The crystal and molecular structure of C.I. Pigment Yellow 83, a superior performance Diarylide Yellow pigment". Dyes and Pigments. 57 (2): 99–106. doi:10.1016/S0143-7208(02)00117-1.

[Werner_Baumann,_Thomas_Rothardt-5] Werner Baumann, Thomas Rothardt (2013), [[1], p. 585, at Google Books Druckerei-chemikalien Daten und Fakten zum Umweltschutz 2., erweiterte und überarbeitete Auflage], Springer-Verlag, p. 585, ISBN 978-3-642-58474-9 {{citation}}: Check |url= value (help)

[Willy_Herbst,_Klaus_Hunger-6] Willy Herbst, Klaus Hunger (2009), [[2], p. 261, at Google Books Industrielle Organische Pigmente Herstellung, Eigenschaften, Anwendung], John Wiley & Sons, p. 261, ISBN 3-527-62496-1 {{citation}}: Check |url= value (help)

[1]

[2]

[3]

[4]

[5]

[6]