Acetoacetamide

Acetoacetamide
	source ↗
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	100.025.250
EC Number	227-774-4;
KEGG	C11106;
PubChem CID	80077;
CompTox Dashboard (EPA)	DTXSID1040164 ;
	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 ammonia¹

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. source ↗

References

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.
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.
Williams, Jonathan W.; Krynitsky, John A. (1941). "Acetoacetanilide". Organic Syntheses. 21: 4. doi:10.15227/orgsyn.021.0004.
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.
K. Hunger. W. Herbst "Pigments, Organic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2012. doi:10.1002/14356007.a20_371

[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.

[Ullmann1-5] 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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