Pigment Yellow 97 is widely used as a yellow

color Color (or colour in English in the Commonwealth of Nations, Commonwealth English; American and British English spelling differences#-our, -or, see spelling differences) is the visual perception based on the electromagnetic spectrum. Though co ...

ant, and is classified as an

arylide yellow Arylide yellow, also known as Hansa yellow and monoazo yellow, is a family of organic compounds used as pigments. They are primarily used as industrial colorants including plastics, building paints and inks. They are also used in artistic oil pai ...

. 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 Acetoacetanilide is an organic compound with the formula CH3C(O)CH2C(O)NHC6H5. It is the acetoacetamide derivative of aniline. It is a white solid that is poorly soluble in water. This chemical and many related compounds (prepared from various ...

component is made from 2,5-dimethoxy-4-chloro

aniline Aniline (From , meaning ' indigo shrub', and ''-ine'' indicating a derived substance) is an organic compound with the formula . Consisting of a phenyl group () attached to an amino group (), aniline is the simplest aromatic amine. It is an in ...

. The azo component is made from a dimethoxyaniline with the sulfonylaminophenyl substituent.he compound is obtained via

acetoacetylation Diketene is an organic compound with the molecular formula , and which is sometimes written as . It is formed by dimerization of ketene, . Diketene is a member of the oxetane family. It is used as a reagent in organic chemistry. It is a colorles ...

of o-tolidine using

diketene Diketene is an organic compound with the molecular formula , and which is sometimes written as . It is formed by dimerization of ketene, . Diketene is a member of the oxetane family. It is used as a reagent in organic chemistry. It is a colorle ...

. The resulting bisacetoacetylated compound is coupled with two equiv of the

diazonium salt Diazonium compounds or diazonium salts are a group of organic compounds sharing a common functional group where R can be any organic group, such as an alkyl or an aryl, and X is an inorganic or organic anion, such as a halide. The parent, comp ...

obtained from 2,4-dichloroaniline.K. Hunger. W. Herbst "Pigments, Organic" in ''Ullmann's Encyclopedia of Industrial Chemistry'', Wiley-VCH, Weinheim, 2012. Although it is often depicted as an azo compound,

X-ray crystallography X-ray crystallography is the experimental science of determining the atomic and molecular structure of a crystal, in which the crystalline structure causes a beam of incident X-rays to Diffraction, diffract in specific directions. By measuring th ...

shows that the molecule exists as a

hydrazone Hydrazones are a class of organic compounds with the structure . They are related to ketones and aldehydes by the replacement of the oxygen =O with the = functional group. They are formed usually by the action of hydrazine on ketones or aldehydes. ...

.{{cite journal , doi=10.1016/j.dyepig.2005.07.001 , title=The crystal structure of CI Pigment Yellow 97, a superior performance Hansa yellow pigment , date=2006 , last1=Christie , first1=R. , last2=Hill , first2=J. , last3=Rosair , first3=G. , journal=Dyes and Pigments , volume=71 , issue=3 , pages=194–198

References

Shades of yellow Chloroarenes Arylide pigments Methoxy compounds Sulfonamides Anilines