Acetoacetanilide

A chemical compound used in the synthesis of dyes and pigments

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Acetoacetanilide is an organic compound with the formula C₁₀H₁₁NO₂. It is a white solid that is used as an intermediate in the synthesis of various dyes and pigments.

Structure and properties

Acetoacetanilide is an amide derived from acetoacetic acid and aniline. It features a carbonyl group adjacent to an amide group, which is characteristic of the acetoacetyl functional group. This structure allows it to participate in various chemical reactions, particularly those involving nucleophilic substitution.

Synthesis

Acetoacetanilide can be synthesized through the acetoacetylation of aniline using diketene as a reagent. The reaction involves the addition of diketene to aniline, forming the acetoacetanilide product. This process is depicted in the following diagram:

Acetoacetylation of aniline with diketene to form acetoacetanilide

Applications

Acetoacetanilide is primarily used as an intermediate in the production of azo dyes and pigments. These dyes are widely used in the textile industry for coloring fabrics. The compound's ability to form stable complexes with metal ions also makes it useful in the production of metal complex dyes.

Safety and handling

As with many chemical compounds, proper safety precautions should be taken when handling acetoacetanilide. It should be stored in a cool, dry place and handled with appropriate personal protective equipment to avoid inhalation or skin contact.

Related pages

• Acetoacetic acid
• Aniline
• Azo dye
• Diketene