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This section provides an overview for ethyl acetoacetate as well as their applications and principles. Also, please take a look at the list of 10 ethyl acetoacetate manufacturers and their company rankings. Here are the top-ranked ethyl acetoacetate companies as of December, 2024: 1.Merck, 2.Oakwood Products, Inc, 3.MedChemExpress.
Table of Contents
Figure 1. Basic Information on Ethyl Acetoacetate
Ethyl acetoacetate is the ethyl ester of acetoacetate, with the chemical formula C6H10O3. Also known as ethyl 3-oxobutanoate, it is a colorless, flammable liquid with a characteristic fruity odor. It is classified as a Class 4 Hazardous Substance and a Class 3 Non-Water Soluble Liquid under the Fire Service Law.
The relatively stable carbanion produced by the action of a base on ethyl acetoacetate is often used in carbon-carbon bond formation reactions.
Ethyl acetoacetate is more reactive than other esters and is used as a raw material for various organic syntheses. Examples include its use as an intermediate in the manufacture of compounds such as antipyretic analgesics, antimalarials, antibiotics, amino acids, and vitamin B.
It also has a fruity odor and is used as a food flavoring agent and in perfumes. Additionally, it can be used in lacquer paints, dye manufacturing, plastic manufacturing, and as an analytical reagent.
Ethyl acetoacetate has a melting point of -45°C, a boiling point of 180.8°C, a flash point of 70°C, and a refractive index of 1.41937 at 20°C. It is soluble in water at 20°C, with 2.86 g dissolving in 100 mL of water. It is extremely soluble in ethanol and acetone.
The hydrogen atom on the methylene moiety at position 2 of ethyl acetoacetate is relatively acidic, with a pKa of 10.7 at 25°C.
Hydrolysis of ethyl acetoacetate with dilute acid or dilute alkali yields carbon dioxide and acetone. However, when reacted with a strong alkali, acetic acid is formed.
Figure 2. Structure of Ethyl Acetoacetate
The empirical formula of ethyl acetoacetate is CH3COCH2COOC2H5. Its molecular weight is 130.14 g/mol, and its density at 25°C is 1.021 g/cm3.
Ethyl acetoacetate exhibits keto-enol tautomerism; at 33°C, the enol form constitutes 15% of the total.
The carbanion, the conjugate base of ethyl acetoacetate, is in resonance with the two enolate structures, allowing the negative charge to be delocalized and stabilized.
Figure 3. Synthesis of Ethyl Acetoacetate
Ethyl acetoacetate is obtained by reacting ethyl acetate with metallic sodium or by condensation of ethyl acetate with sodium ethoxide, whose chemical formula is C2H5ONa. These reactions are known as Claisen condensation.
Industrially, ethyl acetoacetate is produced by treating diketene with ethanol.
Ethyl acetoacetate has an active methylene moiety, forming a relatively stable carbanion with a base. An activated methylene is a methylene group adjacent to two electron-withdrawing groups, such as a carbonyl group.
Compounds with highly acidic activated methylene groups include malonate esters, cyanoacetates, and acetylacetone, offering stability for carbon-carbon bond formation. Examples include acetoacetic ester synthesis and malonic ester synthesis.
Active methylene compounds like ethyl acetoacetate are also used in cross-coupling reactions and Michael addition reactions.
*Including some distributors, etc.
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Oakwood Chemical is based in Estill, South Carolina. The company is a producer of a wide range of organics with particular emphasis on fluorine and sulfur compounds. The company also offers custom synthesis services and bulk quantities upon request. The company has independent operations and operations in collaboration with the University of South Carolina. The company’s suppliers include ChemCollect, Chess, KISHIDA CHEMICAL Co., Ltd., and Tetramer. The company’s featured products include boronic acids and esters, peptide coupling, fluorinated amines, and reagents for synthesis.
MedChemExpress (MCE), is headquartered in Monmouth Junction, New Jersey, and is a supplier of research chemicals and biochemicals for laboratory and scientific use. The company’s product range includes biochemical assay reagents, isotope-labeled compounds, inhibitory antibodies, recombinant proteins, and fluorescent dyes. These products are used in various biopharmaceutical research and development fields, including areas such as infection, cardiovascular diseases, neurodegenerative diseases, diabetes, and autoimmune diseases. The company is ISO 19001 certified and provides testing services within the ISO 17025 framework, offering bulk and custom product services and support for metrological traceability.
Kanto Chemical Co. Inc., founded in 1944 and headquartered in Tokyo, Japan, is a reagent manufacturer with overseas affiliates in other countries, including China, France, USA, Taiwan, and Malaysia. Its product portfolio includes analytical reagents, ionic liquids, Iodine compounds, ultra-pure chemicals, and water analysis kits. The company is also developing regenerative medicine and genetics reagents and has over 50,000 products. It has several certifications, including ISO 9001, acquired in 1994, making it the first Japanese company in the reagent industry. Other certifications are ISO 14001, ISO 13485, and ISO/IEC 17025.
Merck, started in 1668 and based in Darmstadt, Germany, is a supplier of solutions and services for research, development, and manufacture of pharmaceutical and biotechnological drug therapies. The company serves the life science industry and has a broad portfolio of 300,000 products, including biopharmaceutical manufacturing, industrial microbiology, reagent, life science research, and water purification products. It is available in 66 countries, brings together six brands, and has several ISO certifications, including ISO 13485, ISO 14001, ISO 13485, and ISO 50001.
Nacalai Tesque Inc., founded in 1846 and headquartered in Kyoto, Japan, is a manufacturer of research chemicals, fine chemicals, diagnostics, and the related instruments. Some of its products include cytokines, nucleic acid electrophoresis, cell dissociation reagents, and sialic acid-related products, and it also offers custom and bulk service for bulk reagents and cell culture media. The company has more than 50 domestic distributors and several worldwide, including Asia, the Middle East, Oceania, Europe, and Africa. It is ISO 9001 and ISO 9002 certified, while the Kyoto South brand and Tesque factory are ISO 14001 certified.
BOC Sciences is headquartered in Shirley, New York as a brand of BOCSCI Inc. The company is a developer, manufacturer, marketer, and distributor of premium chemicals, emphasizing small molecule synthesis, biosynthesis, purification, and characterization used in academia, pharmaceuticals, biotech, CDMO, material sciences, and agriculture industries, supporting research and production. The company’s products include thousands of inhibitors, nucleotides, metabolites, and isotope-labeled products. The company offers custom synthesis and manufacturing, analytical services, antibody-drug conjugate development, and strain engineering and fermentation services.
Ernesto Ventós S.A. is a company that was established in 1916 in Sant Just Desvern, Spain, specializing in distributing aroma compounds and essential oils to the fragrance and flavoring industries. Ventós is a company that has established solid commercial partnerships with significant raw material producers. As a result, they have become a distinguished agent or distributor of goods for these producers. The company has a wide range of over three thousand products, allowing them to offer efficient just-in-time service to their clients.
CDN Isotopes Inc. has been a provider of deuterium-labelled compounds since its establishment in 1993. Located in Quebec, Canada, they supply researchers in the fields of medicine and science. They have over 3000 products and 98%of their orders are filled from stock. CDN isotopes have international distributors in over 40 countries and have continued to add new products to the market. They aim to provide customers with products at affordable prices while maintaining a large inventory of products.
Ranking as of December 2024
Derivation Method| Rank | Company | Click Share |
|---|---|---|
| 1 | Merck |
36.4%
|
| 2 | Oakwood Products, Inc |
18.2%
|
| 3 | MedChemExpress |
18.2%
|
| 4 | PCW France |
9.1%
|
| 5 | KANTO CHEMICAL CO.,INC. |
9.1%
|
| 6 | nacalai |
9.1%
|
Derivation Method
The ranking is calculated based on the click share within the ethyl acetoacetate page as of December 2024. Click share is defined as the total number of clicks for all companies during the period divided by the number of clicks for each company.Number of Employees
Newly Established Company
Company with a History
*Including some distributors, etc.
*Including some distributors, etc.
| Country | Number of Companies | Share (%) |
|---|---|---|
|
United States of America
|
2 | 25.0% |
|
Japan
|
2 | 25.0% |
France
|
2 | 25.0% |
|
Spain
|
1 | 12.5% |
|
Canada
|
1 | 12.5% |
