5977-14-0 Usage
Description
Acetoacetamide is a β-keto amide that serves as a degradation product of acesulfame-K, a widely used artificial sweetener. It is known for its role in various organic syntheses, particularly in the production of organic dyes and pigments. Acetoacetamide can undergo alkaline hydrolysis to form a salt of acetoacetic acid.
Uses
Used in Organic Synthesis:
Acetoacetamide is used as an intermediate for different organic syntheses, primarily in the production of organic dyestuffs. It is a key component in the synthesis of various N-substituted acetoacetamides, which are primary precursors for several organic dyes and pigments.
Used in Pharmaceutical Industry:
Acetoacetamide is used in the pharmaceutical industry for the synthesis of heterocyclic systems, which are essential in the development of various drugs and pharmaceutical compounds.
Used in Food Industry:
Acetoacetamide has been utilized in studies to assess the stability of artificial sweeteners, such as aspartame and acesulfame-K, during storage. It has also been employed in the analysis of multiple sweeteners and their degradation products in lassi, a popular yogurt-based beverage, using high-performance liquid chromatography (HPLC).
Flammability and Explosibility
Notclassified
Purification Methods
Recrystallise the amide from CHCl3, or Me2CO/pet ether. It also crystallises from pyridine with 4mols of solvent. It is slightly soluble in H2O, EtOH and AcOH but is insoluble in Et2O. The phenylhydrazone has m 128o. [Kato Chem Pharm Bull Jpn 15 921 923 1967, Claisen & Meyer Chem Ber 35 583 1902, Beilstein 3 H 659, 3 I 231, 3 III 1204, 3 IV 1545.]
Check Digit Verification of cas no
The CAS Registry Mumber 5977-14-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,9,7 and 7 respectively; the second part has 2 digits, 1 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 5977-14:
(6*5)+(5*9)+(4*7)+(3*7)+(2*1)+(1*4)=130
130 % 10 = 0
So 5977-14-0 is a valid CAS Registry Number.
InChI:InChI=1/C4H7NO2/c1-3(6)2-4(5)7/h2H2,1H3,(H2,5,7)
5977-14-0Relevant articles and documents
Acid promoted dimerization of β-amino-α,β-unsaturated amides affording bis(functionalized) pyrrolinones
Hirai, Sho,Asahara, Haruyasu,Nishiwaki, Nagatoshi
, p. 5896 - 5898 (2016)
Polysubstituted pyrrolinones were synthesized by the dimerization of 3-amino-2-butenamides via treatment with 0.5 equiv p-TsOH under mild reaction conditions, including oxidation and 1,2-migration of the methyl group. This method is practically advantageo
Syntheses of 5-(alkylaminocarbonyl)-4,6-dimethyl-2-pyridones from N- alkyl-3-oxobutanamides
Furukawa, Isao,Fujisawa, Hironori,Kawazome, Mitsuru,Nakai, Yasuto,Ohta, Tetsuo
, p. 1715 - 1717 (2007/10/03)
1-Alkyl-5-(alkylaminocarbonyl)-4,6-dimethyl-2-pyridones were obtained in high yields from the self-condensation of N-alkyl-3-oxobutanamides in the presence of p-toluenesulfonic acid as a catalyst at 100-110°C for 11-24 hours without solvent.
Reactions of β-Ketoamides. Part 1. Kinetics of Enolisation of Acetoacetamide in Water and of Acetoacetamide and Acetoacetanilide in Ethanol-Water
Hynes, Michael J.,Clarke, Eve M.
, p. 901 - 904 (2007/10/02)
Kinetic results are reported for the rates of enolisation (ke) of acetoacetamide in water and for acetoacetamide and acetoacetanilide in ethanol-water (70:30 v/v) as measured by their rates of halogenation.The effects of nickel(II), zinc(II) and acetate on the rates of enolisation are also described.Unlike β-diketones, the enolisation of β-ketoamides is acid catalysed.The rates of ketonisation (kf) of the two β-ketoamides have been also investigated using stopped-flow spectrophotometry.The keto:enol ratios have been derived using the experimentally measured ke and kf values.
