ethyl acetoacetate (141-97-9)

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Suppliers

• Sigma-Aldrich - ethyl acetoacetate
  38.90 - 2918.30 USD
• Fisher Scientific - Search for ethyl acetoacetate
• TCI - ethyl acetoacetate
  16.00 - 28.00 USD

Most-cited Publications

• Determination of base properties of hydrotalcites: Condensation of benzaldehyde with ethyl acetoacetate (Journal of Catalysis, 1992)
• Production of (+)-(S)-ethyl 3-hydroxybutyrate and (-)-(R)-ethyl 3-hydroxybutyrate by microbial reduction of ethyl acetoacetate. (Helvetica Chimica Acta, 1983)
• Stereoselective reduction of ethyl 4-chloro-3-oxobutanoate by Escherichia coli transformant cells coexpressing the aldehyde reductase and glucose dehydrogenase genes (Applied Microbiology and Biotechnology, 1999)
• Structures of the Reaction Products of Tetraalkoxytitanium with Acetylacetone and Ethyl Acetoacetate (Journal of the American Chemical Society, 1957)
• Gas-phase proton NMR studies of keto-enol tautomerism of acetylacetone, methyl acetoacetate, and ethyl acetoacetate (The Journal of Physical Chemistry, 1985)
• Purification and characterization of NADPH-dependent carbonyl reductase, involved in stereoselective reduction of ethyl 4-chloro-3-oxobutanoate, from Candida magnoliae (Bioscience, Biotechnology, and Biochemistry, 1998)

Areas of Application

Safety

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• H227: Combustible liquid
  Warning Flammable liquids - Category 4

Trends

Alternate Names

• ethyl acetoacetate, 2,4-(14)C-labeled
• ethyl 3-oxobutanoate
• ethyl acetoacetate, 2-(14)C-labeled
• ethyl acetoacetate, 1,2-(14)C-labeled
• ethyl acetoacetate, 3-(14)C-labeled
• ethyl acetoacetate, 1,3-(14)C-labeled
• ethyl acetoacetate, 14C4-labeled
• SMILES
  CCOC(=O)CC(=O)C
• InChIKey
  XYIBRDXRRQCHLP-UHFFFAOYSA-N

External Links

• Pubchem - ethyl acetoacetate
• Wikipedia - ethyl acetoacetate
  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 aminopyrine, 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.

Synthesis

acetoacetic acid  +  Chloroethane (Ester from carboxilic acid(SN2))

Acetonitrile  +  ETHYL CHLOROACETATE (Grignard carbonyl)

3-OXOBUTANOYL CHLORIDE  +  Ethanol (O-acylation)

Reactant  +  dimethyl sulfide (Corey-Kim oxidation of secondary alcohols)

Synthesis of ethyl acetoacetate ›

Similar Compounds

Propyl acetoacetate (1779-60-8)

8 alternate names

3 suppliers

Butyl acetoacetate (591-60-6)

8 alternate names

1 safety hazard

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Isopropyl acetoacetate (542-08-5)

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Ethyl propionylacetate (4949-44-4)

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octyl 3-oxobutanoate (16436-00-3)

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Allyl acetoacetate (1118-84-9)

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METHYL ACETOACETATE (105-45-3)

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Diethyl 1,3-acetonedicarboxylate (105-50-0)

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105-50-0 (105-50-0)

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tert-butyl acetoacetate (1694-31-1)

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Ethyl 3-oxohexanoate (3249-68-1)

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Ethyl 4-bromoacetoacetate (13176-46-0)

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Butyl butyrate (109-21-7)

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Ethyl 4-chloroacetoacetate (638-07-3)

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Ethyl isobutyrylacetate (7152-15-0)

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ethyl 3-oxotetradecanoate (74124-22-4)

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Ethyl 4-ethoxy-3-oxobutyrate (41051-14-3)

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ETHYL BUTYRATE (105-54-4)

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2 safety hazards

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Methyl 3-oxovalerate (30414-53-0)

8 alternate names

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Diethyl 3-oxopimelate (40420-22-2)

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Ethyl 5-methyl-3-oxohexanoate (34036-16-3)

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Ethyl 4,4-dimethyl-3-oxopentanoate (17094-34-7)

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62462-05-9 (62462-05-9)

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Ethyl 2-methylacetoacetate (609-14-3)

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UNII-0KK1QI203I (66841-52-9)

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1830-54-2 (1830-54-2)

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HEXYL BUTYRATE (2639-63-6)

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ethyl 4-oxobutanoate (10138-10-0)

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ethyl 4-hydroxybutanoate (999-10-0)

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Ethyl pentanoate (539-82-2)

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DIBUTYL SUCCINATE (141-03-7)

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ISOAMYL ISOVALERATE (659-70-1)

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delta-Valerolactone (542-28-9, 26354-94-9)

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ethyl 4,4-difluoro-3-oxobutanoate (352-24-9)

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Methyl 3-oxohexanoate (30414-54-1)

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6-Hexanolactone (24980-41-4, 502-44-3)

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Butyl hexanoate (626-82-4)

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Methyl 4-methoxyacetoacetate (41051-15-4)

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Dipropyl succinate (925-15-5)

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Tetronic acid (4971-56-6)

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BUTYL STEARATE (123-95-5, 68154-28-9)

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Heptanolactone (539-87-7)

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Oxacyclohexadecan-2-one (106-02-5)

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Heptyl heptanoate (624-09-9)

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Methyl 3-oxotetradecanoate (22348-97-6)

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DIETHYL SUCCINATE (123-25-1, 68989-32-2)

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ETHYL ISOVALERATE (108-64-5)

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4-Ethoxy-4-oxobutanoic acid (1070-34-4)

8 alternate names

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Methyl 4-chloroacetoacetate (32807-28-6)

8 alternate names

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Adipic acid monoethyl ester (626-86-8)

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Ethyl 6-hydroxyhexanoate (5299-60-5)

8 alternate names

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DIETHYL GLUTARATE (68989-30-0, 818-38-2, 68989-31-1)

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Ethyl 4-chlorobutyrate (3153-36-4)

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DIETHYL ADIPATE (141-28-6, 68201-71-8, 68989-28-6)

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Ethyl hydrogen glutarate (1070-62-8)

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ethyl 3-cyclopropyl-3-oxopropanoate (24922-02-9)

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Ethyl 3-hydroxybutyrate (35608-64-1, 5405-41-4)

8 alternate names

1 safety hazard

3 suppliers

ETHYL LEVULINATE (539-88-8)

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1,6-Dioxacycloheptadecan-7-one (6707-60-4)

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Propyl dodecanoate (3681-78-5)

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Diethyl oxalacetate (108-56-5)

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3 suppliers

55107-14-7 (55107-14-7)

8 alternate names

3 suppliers

Oxepane-2,7-dione (2035-75-8)

8 alternate names

3 suppliers

Ethyl 2-ethylacetoacetate (607-97-6)

8 alternate names

3 suppliers

Ethyl 4-bromobutyrate (2969-81-5)

8 alternate names

3 suppliers

Ethyl 3-cyanopropanoate (10137-67-4)

8 alternate names

3 suppliers

ETHYL PALMITATE (628-97-7)

8 alternate names

3 suppliers

ETHYL DECANOATE (110-38-3)

8 alternate names

3 suppliers

Ethyl Hydrogen Pimelate (33018-91-6)

8 alternate names

3 suppliers

ETHYL NONANOATE (123-29-5)

8 alternate names

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Ethyl dodecanoate (106-33-2)

8 alternate names

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DIETHYL SUBERATE (2050-23-9)

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Ethyl tetradecanoate (124-06-1)

8 alternate names

3 suppliers

ETHYL UNDECANOATE (627-90-7)

8 alternate names

3 suppliers

ETHYL TRICOSANOATE (18281-07-7)

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Ethyl 6-oxononanoate (4144-59-6)

8 alternate names

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Ethyl 6-oxooctanoate (4233-58-3)

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6937-16-2 (6937-16-2)

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GLUTARIC ANHYDRIDE (108-55-4)

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Palmitic anhydride (623-65-4)

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Stearic anhydride (638-08-4)

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Lauric anhydride (645-66-9)

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Octanoic anhydride (623-66-5)

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ethyl 3-cyclohexyl-3-oxopropanoate (15971-92-3)

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3 suppliers

Ethyl 4,4,4-trichloroacetoacetate (3702-98-5)

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Ethyl hydrogen malonate (1071-46-1)

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Ethyl potassium malonate (6148-64-7)

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3 suppliers

Diisononyl adipate (33703-08-1)

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6-Methylheptyl palmitate (1341-38-4, 106-05-8)

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8-methylnonyl nonanoate (109-32-0)

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Ethyl 4,4,4-trifluoroacetoacetate (372-31-6)

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Dioctyl malonate (16958-88-6)

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Butyl acetate (123-86-4)

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3 safety hazards

3 suppliers

Ethyl tert-butylacetate (5340-78-3)

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3 suppliers

Ethyl 5-bromovalerate (14660-52-7)

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Ethyl diacetoacetate (603-69-0)

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3 suppliers

DIETHYL MALONATE (105-53-3)

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2 safety hazards

3 suppliers

Ethyl 5-oxodecanoate (93919-00-7)

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2-Methylbutyric anhydride (1519-23-9)

8 alternate names

3 suppliers

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ethyl acetoacetate

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