Ethyl acetoacetate

Base Information

• Chemical Name: Ethyl acetoacetate
• CAS No.: 141-97-9
• Molecular Formula: C6H10O3
• Molecular Weight: 130.144
• Hs Code.: 29183000
• European Community (EC) Number: 205-516-1
• ICSC Number: 1024
• NSC Number: 8657
• UN Number: 1993
• UNII: IZP61H3TB1
• DSSTox Substance ID: DTXSID2027092
• Nikkaji Number: J4.493H
• Wikipedia: Ethyl_acetoacetate
• Wikidata: Q47192
• Metabolomics Workbench ID: 44759
• ChEMBL ID: CHEMBL169176
• Mol file: 141-97-9.mol

Synonyms:ethyl 3-oxobutanoate;ethyl acetoacetate;ethyl acetoacetate, 1,2-(14)C-labeled;ethyl acetoacetate, 1,3-(14)C-labeled;ethyl acetoacetate, 14C4-labeled;ethyl acetoacetate, 2,4-(14)C-labeled;ethyl acetoacetate, 2-(14)C-labeled;ethyl acetoacetate, 3-(14)C-labeled;ethyl beta-ketobutyrate

Chemical Property of Ethyl acetoacetate

Chemical Property:

• Appearance/Colour: Colourless liquid
• Vapor Pressure: 1 mm Hg ( 28.5 °C)
• Melting Point: -43 °C
• Refractive Index: n20/D 1.419
• Boiling Point: 180.6 °C at 760 mmHg
• PKA: 11(at 25℃)
• Flash Point: 67 °C
• PSA: 43.37000
• Density: 1.021 g/cm³
• LogP: 0.52860
• Storage Temp.: Store below +30°C.
• Solubility.: 116 g/L (20°C)
• Water Solubility.: 116 g/L (20 ºC)
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 130.062994177
• Heavy Atom Count: 9
• Complexity: 118
• Transport DOT Label: Flammable Liquid

Purity/Quality:

99% ^*data from raw suppliers

Ethyl acetoacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Esters, Other
• Canonical SMILES: CCOC(=O)CC(=O)C
• Recent ClinicalTrials: Effects of Essential Amino Acid-enriched Whey and Carbohydrate Co-ingestion on Protein Kinetics
• Inhalation Risk: A harmful contamination of the air will not or will only very slowly be reached on evaporation of this substance at 20 °C; on spraying or dispersing, however, much faster.
• Effects of Short Term Exposure: The substance is irritating to the eyes, skin and respiratory tract.
• Description: The organic compound ethyl acetoacetate (EAA) is the ethyl ester of acetoacetic acid. It is mainly used as a chemical intermediate in the production of a wide variety of compounds, such as amino acids, analgesics, antibiotics, antimalarial agents, antipyrine and amino pyrine, and vitamin B1; as well as the manufacture of dyes, inks, lacquers, perfumes, plastics, and yellow paint pigments. Alone, it is used as a flavoring for food.
• Uses: Ethyl acetoacetate (EAA) is used as starting material for the syntheses of alpha-substituted acetoacetic esters and cyclic compounds, e.g. pyrazole, pyrimidine and coumarin derivatives as well as intermediate for vitamins and pharmaceuticals. Product Data Sheet Ethyl acetoacetate is used as an intermediate in organic synthesis and as a co-promoter for unsaturated polyester resins. It is widely used in the production of dyes, inks, perfumes, plastics and flavoring agents. It is an important starting material for the syntheses of alpha-substituted acetoacetic esters and cyclic compounds like pyrazole, pyrimidine and coumarin derivatives. It acts as an intermediate in the synthesis of vitamins and pharmaceuticals. It finds application as a formaldehyde scavenger.

Technology Process of Ethyl acetoacetate

There total 250 articles about Ethyl acetoacetate 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: 90.0%

(2-Methyl-1,3-dithiolan-2-yl)essigsaeure-ethylester (66278-17-9) → ethyl acetoacetate (141-97-9) + ethane-1,2-dithiol (540-63-6)

Guidance literature:

With magnesium(II) perchlorate; water; methylene green; In acetonitrile; Irradiation;

DOI:10.1016/S0040-4039(00)61086-9

Reference yield: 87.0%

isonicotinic acid ethylester (1570-45-2) + ethyl acetate (141-78-6) → ethyl 3-oxo-3-(4-pyridyl)propanoate (26377-17-3) + ethyl acetoacetate (141-97-9)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at -40 ℃; for 0.333333h; Inert atmosphere;

DOI:10.1016/j.bmcl.2012.04.008

Reference yield: 61.0%

1,2-diamino-benzene (95-54-5) + ethyl 2-acetylacetoacetate (603-69-0) → 2-Methyl-1H-benzimidazole (615-15-6) + ethyl acetoacetate (141-97-9)

Guidance literature:

In ethanol; Heating;

DOI:10.1007/BF00961931

upstream raw materials:

4-methyleneoxetan-2-one

ethanol

4,6-dimethyl-tetrahydro-pyran-2-one

ethyl acetate

Downstream raw materials:

3-acetyl-7-methoxycoumarin

4-carbethoxy-3-methyl-2-cyclohexen-1-one

2,4-diethoxycarbonyl-5-hydroxy-5-methyl-3-phenylcyclohexanone

2,4-diacetyl-3-styryl-glutaric acid diethyl ester

Refernces

• 1、 Snell,McElvain. "-". . . Retrieved 1933.
• 2、 Kadam, Shivaji S.,Maier, Lukas,Kostakis, Ioannis,Pouli, Nicole,Tousek, Jaromir,Necas, Marek,Marakos, Panagiotis,Marek, Radek. "Synthesis and tautomerism of substituted pyrazolo[4,3-c]pyrazoles". . p. 6811 - 6822. Retrieved 2013.
• 3、 Scheibler,Ziegner. "-". . p. 789,798. Retrieved 1922.
• 4、 Scheibler. "-". . p. 6. Retrieved 1923.
• 5、 Orsini, F.,Pelizzoni, F.,Ricca, G.. "REFORMATSKY INTERMEDIATE. A C-METALLED SPECIES.". . p. 3945 - 3948. Retrieved 1982.
• 6、 Lu, Jie,Han, Buxing,Yan, Haike. "UV-Vis spectroscopic studies of solute-solvent and solute-cosolvent interactions in supercritical carbon dioxide". . p. 3269 - 3276. Retrieved 1999.
• 7、 Cocivera,M. et al.. "-". . p. 7362 - 7366. Retrieved 1976.
• 8、 Matsumoto et al.. "-". . p. 2731. Retrieved 1973.
• 9、 Movassaghi, Mohammad,Ondrus, Alison E.. "Palladium-catalyzed synthesis of N-vinyl pyrroles and indoles". . p. 8638 - 8641. Retrieved 2005.
• 10、 Venkatesh, Telugu,Mainkar, Prathama S.,Chandrasekhar, Srivari. "Diastereoselective Formal Synthesis of Polycyclic Meroterpenoid (±)-Cochlearol A". . p. 5412 - 5416. Retrieved 2021.