Pigment Yellow 83

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

Pigment Yellow 83

Names
Other names Enceprint Yellow 1780, Homapol Yellow PO-227
Identifiers
CAS Number	5567-15-7 Y
3D model (JSmol)	Interactive image
ChemSpider	20428
ECHA InfoCard	100.024.491
EC Number	226-939-8
PubChem CID	21733
UNII	67HO7X7FV3 Y
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

The compound is synthesized 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] As confirmed by X-ray crystallography, the compound exists as a bis(keto-hydrazide) tautomer, not a true diazo compound.^[2]