Acetoacetamide

Last updated
Acetoacetamide
Acetoacetamide structure.svg
Names
Other names
3-oxobutanamide, 3-oxobutyramide
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.025.250 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 227-774-4
KEGG
PubChem CID
  • 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
Appearancewhite 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).

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]

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

References

  1. ↑ Miller, Raimund; Abaecherli, Claudio; Said, Adel; Jackson, Barry (2001). "Ketenes". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a15_063. ISBN   978-3-527-30385-4.
  2. ↑ George, V.; Arora, S.; Wadhwa, B. K.; Singh, A. K. (August 2010). "Analysis of multiple sweeteners and their degradation products in lassi by HPLC and HPTLC plates". Journal of Food Science and Technology. 47 (4): 408–413. doi:10.1007/s13197-010-0067-4. ISSN   0022-1155. PMC   3551007 . PMID   23572661.
  3. ↑ Williams, Jonathan W.; Krynitsky, John A. (1941). "Acetoacetanilide". Organic Syntheses. 21: 4. doi:10.15227/orgsyn.021.0004.
  4. ↑ Jaffe, Edward E. (2004). "Pigments, Organic". Kirk-Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.151807011001060605.a01.pub2. ISBN   978-0-471-48494-3.
  5. ↑ K. Hunger. W. Herbst "Pigments, Organic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2012. doi : 10.1002/14356007.a20_371


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