ChemicalBook > Product Catalog > Organic Chemistry > Carboxylic acids and derivatives > Carboxylic acid esters and derivatives > Ethyl acetoacetate
Ethyl acetoacetate Chemical Properties
- Melting point:−43 °C(lit.)
- Boiling point:181 °C(lit.)
- Density 1.029 g/mL at 20 °C(lit.)
- vapor density 4.48 (vs air)
- vapor pressure 1 mm Hg ( 28.5 °C)
- refractive index n
- FEMA 2415 | ETHYL ACETOACETATE
- Flash point:185 °F
- storage temp. Store below +30°C.
- solubility 116 g/L (20°C)
- pka11(at 25℃)
- form Liquid
- color APHA: ≤15
- Specific Gravity1.027～1.035 (20/4℃)
- Relative polarity0.577
- OdorAgreeable, fruity.
- PH4.0 (110g/l, H2O, 20℃)
- explosive limit1.0-54%(V)
- Water Solubility 116 g/L (20 ºC)
- JECFA Number595
- Merck 14,3758
- BRN 385838
- Stability:Stable. Incompatible with acids, bases, oxidizing agents, reducing agents, alkali metals. Combustible.
- CAS DataBase Reference141-97-9(CAS DataBase Reference)
- NIST Chemistry ReferenceButanoic acid, 3-oxo-, ethyl ester(141-97-9)
- EPA Substance Registry SystemEthyl acetoacetate (141-97-9)
- Hazard Codes Xi
- Risk Statements 36
- Safety Statements 26-24/25
- RIDADR UN 1993
- WGK Germany 1
- RTECS AK5250000
- Autoignition Temperature580 °F
- TSCA Yes
- HazardClass 3.2
- PackingGroup III
- HS Code 29183000
- Hazardous Substances Data141-97-9(Hazardous Substances Data)
- ToxicityLD50 orally in rats: 3.98 g/kg (Smyth)
Ethyl acetoacetate Usage And Synthesis
- DescriptionThe 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.
- Chemical PropertiesEthyl acetoacetate has a characteristic ether-like, fruity, pleasant, refreshing odor.
- Chemical PropertiesEthyl 3-Oxobutanoate is a colorless liquid with a fruity, ethereal, sweet odor reminiscent of green apples. It is used to create fresh, fruity top notes in feminine fine fragrances. Ethyl acetoacetate occurs in flavors of natural materials such as coffee, strawberries, and yellow passion fruits.
- OccurrenceNaturally occurring in strawberry, coffee, sherry, passion fruit juice (yellow), babaco fruit (Carica pentagona Heilborn) and bread.
- UsesEthyl 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
- DefinitionThis compound is a tautomer at room temperature consisting of about 93% keto form and 7% enol form.
- Production MethodsEthyl acetoacetate is manufactured through a reaction of high-purity ethyl acetate with sodium, followed by neutralization with sulfuric acid.
- PreparationEthyl acetoacetate is produced industrially by treatment of diketene with ethanol.
The preparation of ethyl acetoacetate is a classic laboratory procedure . It is prepared via the Claisen condensation of ethyl acetate. Two moles of ethyl acetate condense to form one mole each of ethyl acetoacetate and ethanol.
- Aroma threshold valuesDetection: 520 ppb. Aroma characteristics at 10%: sweet fruity apple, fermented, slightly fusel-like and rummy, fruity banana with tropical nuances.
- Taste threshold valuesTaste characteristics at 100 ppm: fruity banana, apple and white grape with slightly green estry and tropical nuances.Taste characteristics at 300 ppm: estery, fatty, fruity and tutti-frutti
- Synthesis Reference(s)The Journal of Organic Chemistry, 58, p. 793, 1993 DOI: 10.1021/jo00055a046
- General DescriptionA colorless liquid with a fruity odor. Flash point 185°F. Boiling point 365°F. May cause adverse health effects if ingested or inhaled. May irritate to skin, eyes and mucous membranes. Used in organic synthesis and in lacquers and paints.
- Air & Water ReactionsFlammable.
- Reactivity ProfileEthyl acetoacetate, a beta-keto ester, is more reactive than many esters. Undergoes an exothermic cleavage reaction in the presence of concentrated base. Reacts with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides. Mixing with 2,2,2-tris(bromomethyl)ethanol and zinc led to an explosion [US Patent 3 578 619, Crotonaldehyde may rapidly polymerize with Ethyl acetoacetate (Soriano, D.S. et al. 1988. Journal of Chemical Education 65:637.).1971].
- HazardToxic by ingestion and inhalation; irritant to skin and eyes.
- Health HazardLiquid may cause mild irritation of eyes.
- Chemical ReactivityReactivity with Water No reaction; Reactivity with Common Materials: No reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.
- Chemical ReactivityEthyl acetoacetate is subject to Keto - enol tautomerism. Ethyl acetoacetate is often used in the acetoacetic ester synthesis similar to diethyl malonate in the malonic ester synthesis or the Knoevenagel condensation. The protons alpha to carbonyl groups are acidic, and the resulting carbanion can undergo nucleophilic substitution. A subsequent thermal decarboxylation is also possible.Similar to the behavior of acetylacetone, the enolate of ethyl acetoacetate can also serve as a bidentate ligand. For example, it forms purple coordination complexes with iron (III) salts :
Ethyl acetoacetate can also be reduced to ethyl 3-hydroxy butyrate.
- Safety Profileeye irritant. Combustible liquid when exposed to heat or flame; can react with oxidzing materials. Explosive reaction when heated with Zn + tribromoneopentyl alcohol or 2,2,2 tris(bromomethy1)ethanol. To fight fire, use alcohol foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes. See also ESTERS.
- Chemical SynthesisEthyl acetoacetate is a mixture of two tautomer forms: the enolic and the ketonic; the liquid ester at equilibrium contains approximately 70% of the enolic form. It is prepared by Claisen condensation of ethyl acetate in the presence of sodium ethylate; also by reacting diketene with ethanol in the presence of sulfuric acid or triethylamine and sodium acetate, with or without solvent.
- Purification MethodsShake the ester with small amounts of saturated aqueous NaHCO3 (until no further effervescence), then with water. Dry it with MgSO4 or CaCl2 and distil it under reduced pressure. [Beilstein 3 IV 1528.]
Ethyl acetoacetate Preparation Products And Raw materials
- Raw materialsEtanolSodiumSodium ethoxideAcetyl keteneMETHANE
- Preparation Products2,4-DIMETHYLQUINOLINE-3-CARBOXYLIC ACID4-CHLORO-2,6-DIMETHYL-NICOTINIC ACIDETHYL 2-HYDROXY-4-METHYL-5-PYRIMIDINECARBOXYLATEBISPYRAZOLONEETHYL 4-CHLORO-2,6-DIMETHYLPYRIDINE-3-CARBOXYLATETIADINIL1-Bromo-5-hexanone3-CHLORO-4-METHYL-7-HYDROXYCOUNMARIN5,7-Dihydroxy-4-methylcoumarin5-METHYL-1-PHENYL-1H-PYRAZOLE-4-CARBOXYLIC ACID7,8-DIHYDROXY-4-METHYLCOUMARIN6-TERT-BUTYL-4-METHYLCOUMARIN2-Amino-6-methyl-4-pyrimidinol4,7-DIMETHYLCOUMARIN1,3-Dimethyl-5-hydroxypyrazole4-Chloro-6-methyl-2-(methylthio)pyrimidine(5-METHYL-1-PHENYL-1H-PYRAZOL-4-YL)METHANOL7-Acetoxy-4-methylcoumarinPentoxifylline4-MethylumbelliferoneDisperse Yellow H-4GLETHYL 2,4-DIMETHYLQUINOLINE-3-CARBOXYLATE3-METHYL-5-PHENYL-4-ISOXAZOLECARBOXYLIC ACIDPHENOXYACETIC ACIDChrysinCloricromeneethyl 2-[2-(diethylamino)ethyl]acetoacetate ETHYL 5-METHYL-1-PHENYL-1H-PYRAZOLE-4-CARBOXYLATE6-Methyl-2-(methylthio)pyrimidin-4-olETHYL 2-ACETYL-3-OXO-HEXANOATE4-HYDROXY-2-METHYLQUINOLINE3-ETHOXYCARBONYL-5,6-DIHYDRO-2-METHYL-4H-PYRAN1-(6-CHLORO-2-HYDROXY-4-PHENYL-QUINOLIN-3-YL)-ETHANONE4-MethylcumarinAcetoacetic AcidEthyl 3-anilinobut-2-enoateEthyl 3-hydroxybutyrateETHYL 2-(HYDROXYIMINO)-3-OXOBUTANOATEN-Phenylglycine potassium salt3-Ethyl-4-methyl-3-pyrrolin-2-one
- Ethoxyamine hydrochloride Acetohydroxamic acid Isopropyl acetoacetate Methyl acetoacetate tert-Butyl acetoacetate 2-Ethoxyethanol Acetoacetic Acid Acetoxyacetic acid TRIS(TRIMETHYLSILYL) PHOSPHATE Trinexapac-ethyl Ethanol BUTYL OLEATE Ethyl acetate Ethyl formate Olibanum oil Ethylparaben Diethyl ether Ethyl 2-chloroacetoacetate
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