Acetoacetamide

Base Information

• Chemical Name: Acetoacetamide
• CAS No.: 5977-14-0
• Molecular Formula: C4H7NO2
• Molecular Weight: 101.105
• Hs Code.: 2924.29
• European Community (EC) Number: 227-774-4
• NSC Number: 632231
• UNII: 6O9U7CFY0T
• DSSTox Substance ID: DTXSID1040164
• Nikkaji Number: J26.750C
• Wikidata: Q18471170
• Metabolomics Workbench ID: 51744
• ChEMBL ID: CHEMBL1984636
• Mol file: 5977-14-0.mol

Synonyms:Acetoacetamide(6CI,7CI,8CI);3-Oxobutanamide;3-Oxobutyramide;Acetoacetic acid amide;Acetylacetamide;NSC 632231;a-Acetylacetamide;

Chemical Property of Acetoacetamide

Chemical Property:

• Appearance/Colour: White to yellowish crystals
• Vapor Pressure: 0.0066mmHg at 25°C
• Melting Point: 53-56 °C(lit.)
• Refractive Index: 1.435
• Boiling Point: 271 °C at 760 mmHg
• PKA: 12.38±0.46(Predicted)
• Flash Point: 80.6 °C
• PSA: 60.16000
• Density: 1.093 g/cm³
• LogP: 0.15110
• Storage Temp.: Refrigerator
• Solubility.: water: soluble1g/10 mL, clear, colorless
• Water Solubility.: 1000g/L at 20℃
• XLogP3: -1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 101.047678466
• Heavy Atom Count: 7
• Complexity: 97.9

Purity/Quality:

99.9% ^*data from raw suppliers

Acetoacetamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)CC(=O)N
• Uses: Acetoacetamide is used as intermediate for different organic syntheses, mainly organic dyestuffs. Product Data Sheet Acetoacetamide was used in a study to assess the stability of artificial sweeteners- aspartame, acesulfame-K and binary sweetener blend of aspartame x acesulfame-K during storage. Acetoacetamide was also used in analysis of multiple sweeteners and their degradation products in lassi by HPLC. Acetoacetamide is a β-keto amide commonly used in building heterocyclic systems. It can be used in synthesizing various N-substituted acetoacetamides, that are primary precursors for several organic dyes and pigments.

Technology Process of Acetoacetamide

There total 20 articles about Acetoacetamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 59.0%

ethyl acetoacetate (141-97-9) → acetoacetamido (5977-14-0)

Guidance literature:

With ammonia; In 1,4-dioxane; at 30 ℃; for 24h; Candida antarctica lipase;

DOI:10.1016/S0040-4039(00)61751-3

Reference yield: 48.0%

3-propylamino-2-butenamide → acetoacetamido (5977-14-0) + 1-propyl-2,5-dimethyl-3-oxo-2,3-dihydro-1H-pyrrole-2,4-dicarboxiamide

Guidance literature:

With oxygen; toluene-4-sulfonic acid; In benzene; at 60 ℃; for 24h;

DOI:10.1016/j.tetlet.2016.11.068

Reference yield:

4-methyleneoxetan-2-one (674-82-8,2130-41-8) → acetoacetamido (5977-14-0)

Guidance literature:

With ammonia; In diethyl ether;

DOI:10.1021/jo01037a009

upstream raw materials:

cyclobutane-1,3-dione

ethyl acetoacetate

acetoacetic acid methyl ester

4-methyleneoxetan-2-one

Downstream raw materials:

4-acetyl-pyrrolidine-2,3,5-trione

4,7-dihydro-5-methyl-7-oxo[1,2,4]triazolo[1,5-a]pyrimidine

3-acetyl-5-hydroxy-4,5-dimethyl-1,5-dihydro-pyrrol-2-one

2-methyl-3-oxobutanamide

Refernces

• 1、 Hilgenkamp, Ramona,Zercher, Charles K. "Zinc carbenoid-mediated chain extension of β-keto amides". . p. 8793 - 8800. Retrieved 2007/10/03.
• 2、 Samet,Kislyi,Chernyshova,Reznikov,Ugrak,Semenov. "Synthesis of heterocyclic systems with carbohydrate fragment: 2. Stereoselective synthesis of tetrahydropyridones by reaction of levoglucosenone with amides of α-methylene-active acids". . p. 393 - 398. Retrieved 2007/10/03.