Acetoacetamide

Chemical compound From Wikipedia, the free encyclopedia

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]

Quick facts Names, Identifiers ...
Acetoacetamide
Names
Other names
3-oxobutanamide, 3-oxobutyramide
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.025.250 Edit this at Wikidata
EC Number
  • 227-774-4
KEGG
  • InChI=1S/C4H7NO2/c1-3(6)2-4(5)7/h2H2,1H3,(H2,5,7)
    Key: GCPWJFKTWGFEHH-UHFFFAOYSA-N
  • CC(=O)CC(=O)N
Properties
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).
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It results from degradation of the sweetner acesulfame potassium.[2]

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.

References

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