Acetoacetamide

Acetoacetamide
	File:Acetoacetamide structure.svg
Names
	Other names 3-oxobutanamide, 3-oxobutyramide
Identifiers
CAS Number	5977-14-0;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:28515;
ChEMBL	ChEMBL1984636;
ChemSpider	72327;
ECHA InfoCard	Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
EC Number	227-774-4;
E number	Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).
KEGG	C11106;
PubChem CID	80077;
CompTox Dashboard (EPA)	{{#property:P3117}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).;
	InChI InChI=1S/C4H7NO2/c1-3(6)2-4(5)7/h2H2,1H3,(H2,5,7) Key: GCPWJFKTWGFEHH-UHFFFAOYSA-N;
	SMILES CC(=O)CC(=O)N;
Properties
Chemical formula	C4H7NO2
Molar mass	101.105 g·mol−1
Appearance	white solid
Melting point	53-56
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Acetoacetamide is an organic compound with the formula CH₃COCH₂CONH₂. It is the amide of acetoacetic acid. It is produced by treating diketene with aqueous ammonia^[1]

It results from degradation of the sweetner acesulfame potassium.^[2]

Related compounds

Acetoacetanilide (CH₃COCH₂CONH₂) is the N-phenyl derivative of acetoacetamide. It is also prepared from diketene.^[3] It and various derivatives are used in the production of organic pigments called arylide yellows, one example being Pigment Yellow 74. Many analogues have been prepared.^[4] To make the dyes, acetoacetanilides are coupled to diazonium salts, "azo coupling".^[5]

Acetoacetylation with diketene followed by diazo coupling. The ketohydrazone tautomer is shown.

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