Acetoacetanilide is an organic compound with the formula CH₃C(O)CH₂C(O)NHC₆H₅. It is the acetoacetamide derivative of

aniline Aniline is an organic compound with the formula C6 H5 NH2. Consisting of a phenyl group attached to an amino group, aniline is the simplest aromatic amine In organic chemistry, an aromatic amine is an organic compound consisting of an aroma ...

. It is a white solid that is poorly soluble in water. It and many related compounds (prepared from various aniline derivatives) are used in the production of organic

pigment A pigment is a colored material that is completely or nearly insoluble in water. In contrast, dyes are typically soluble, at least at some stage in their use. Generally dyes are often organic compounds whereas pigments are often inorganic compo ...

s called arylide yellows.

Preparation and reactions

Acetoacetanilide is prepared by

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 colorl ...

of aniline 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 ...

. To make the dyes, acetoacetanilides are coupled to diazonium salts, " azo coupling".K. Hunger. W. Herbst "Pigments, Organic" in ''Ullmann's Encyclopedia of Industrial Chemistry'', Wiley-VCH, Weinheim, 2012. {{doi, 10.1002/14356007.a20_371

References

Anilides

Preparation and reactions

See also

References