Pigment Yellow 97

Last updated
Pigment Yellow 97
PigYellow97CorrectTaut.svg
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.032.195 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 235-427-3
PubChem CID
UNII
  • InChI=1S/C26H27ClN4O8S/c1-15(32)25(26(33)28-18-12-20(36-2)17(27)11-21(18)37-3)30-29-19-13-23(39-5)24(14-22(19)38-4)40(34,35)31-16-9-7-6-8-10-16/h6-14,25,31H,1-5H3,(H,28,33)
    Key: WNWZKKBGFYKSGA-UHFFFAOYSA-N
  • CC(=O)C(C(=O)NC1=CC(=C(C=C1OC)Cl)OC)N=NC2=CC(=C(C=C2OC)S(=O)(=O)NC3=CC=CC=C3)OC
Properties
C26H27ClN4O8S
Molar mass 591.03 g·mol−1
Appearanceyellow solid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Pigment Yellow 97 is widely used as a yellow colorant, and is classified as an arylide yellow. It is distinguished by the presence of a sulfonylaminophenyl group, which renders the material particularly insoluble (resistant to migration). It is derived from two fairly complicated precursors. The acetoacetanilide component is made from 2,5-dimethoxy-4-chloroaniline. The azo component is made from a dimethoxyaniline with the sulfonylaminophenyl substituent. The compound is obtained via acetoacetylation of o-tolidine using diketene. The resulting bisacetoacetylated compound is coupled with two equiv of the diazonium salt obtained from 2,4-dichloroaniline. [1] Although it is often depicted as an azo compound, X-ray crystallography shows that the molecule exists as a hydrazone. [2]

References

  1. ↑ K. Hunger. W. Herbst "Pigments, Organic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2012. doi : 10.1002/14356007.a20_371
  2. ↑ Christie, R.; Hill, J.; Rosair, G. (2006). "The crystal structure of CI Pigment Yellow 97, a superior performance Hansa yellow pigment". Dyes and Pigments. 71 (3): 194–198. doi:10.1016/j.dyepig.2005.07.001.
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