Acetoacetanilide

Chemical properties

White to off-white powder

The Uses of Acetoacetanilide

Acetoacetanilide is used as intermediate for the manufacture of organic pigments and dyestuffs.

The Uses of Acetoacetanilide

Acetoacetanilide (AAA) flakes is used as an intermediate for the manufacture of organic pigments and dyestuffs. For further information consult the Product information sheet. Product Data Sheet

The Uses of Acetoacetanilide

Acetoacetanilide may be used to synthesize:

• azo pigments
• acetoacetanilido-4-aminoantipyrine (Schiff base)
• 6-aryl-2-methyl-4-oxo-N,N′-diphenyl-2-cyclohexene-1,3-dicarboxamides
• photoluminescent lanthanide complexes

Synthesis Reference(s)

The Journal of Organic Chemistry, 56, p. 1713, 1991 DOI: 10.1021/jo00005a013

General Description

White crystalline solid.

Air & Water Reactions

Water insoluble.

Reactivity Profile

Organic amides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides with strong reducing agents. Amides are very weak bases (weaker than water). Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx). Ketones are reactive with many acids and bases liberating heat and flammable gases (e.g., H2). The amount of heat may be sufficient to start a fire in the unreacted portion of the ketone. Ketones react with reducing agents such as hydrides, alkali metals, and nitrides to produce flammable gas (H2) and heat. Ketones are incompatible with isocyanates, aldehydes, cyanides, peroxides, and anhydrides. They react violently with aldehydes, HNO3, HNO3 + H2O2, and HClO4.

Health Hazard

ACUTE/CHRONIC HAZARDS: Acetoacetanilide is a weak allergen. When heated to decomposition it emits toxic fumes.

Fire Hazard

Acetoacetanilide is combustible.

Safety Profile

Poison by intraperitoneal route. Moderately toxic by ingestion. A weak allergen. See also ACETANILIDE. Combustible when exposed to heat or flame. See ANILINE and CYANIDE for disaster hazard. When heated to decomposition it emits toxic NOx, fumes. To fight fire, use alcohol foam, water mist, CO2, dry chemical.

Purification Methods

Crystallise the anilide from H2O, aqueous EtOH or pet ether (b 60-80o). [Williams & Krynitsky Org Synth Coll Vol III 10 1955.]