Acetoacetanilide

This chemical and many related compounds (prepared from various aniline derivatives) are used in the production of organic pigments called arylide yellows, one example being Pigment Yellow 74.

Acetoacetanilide crystallizes as the keto-amide tautomer according to X-ray crystallography.

The molecules are linked by intermolecular hydrogen bonds, which allows the benzoyl ketone to rotate out of the plane of the amide.

[1] For the general case of substituted acetoanilides, substituents on the aryl ring affect the balance of intra- vs intermolecular hydrogen bonding.

[6] In the presence of sulfuric acid, acetoacetanilide dehydrates to give 4-methyl-2-quinolone.

NFPA 704 four-colored diamond Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen Special hazards (white): no code
Acetoacetylation with diketene followed by diazo coupling. The ketohydrazone tautomer is shown.