Acetoacetamide

Acetoacetamide
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;
UNII	6O9U7CFY0T ;
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 ammonia

It results from degradation of the sweetener acesulfame potassium.

Related compounds

Acetoacetanilide (CH₃COCH₂CONH₂) is the N-phenyl derivative of acetoacetamide. It is also prepared from diketene. 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. To make the dyes, acetoacetanilides are coupled to diazonium salts, "azo coupling".

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

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[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