| Identification | More | [Name]
Ethyl acetoacetate | [CAS]
141-97-9 | [Synonyms]
3-KETOBUTANOIC ACID ETHYL ESTER
3-OXOBUTANOIC ACID ETHYL ESTER
3-OXOBUTYRIC ACID ETHYL ESTER
ACE
ACETOACETIC ACID ETHYL ESTER
ACETOACETIC ESTER
ACETOACETIC ESTER (ETHYL)
ACETOACETIC ETHER
AKOS BBS-00004335
DIACETIC ETHER
EAA
ETHYL 3-KETOBUTANOATE
ETHYL 3-OXOBUTANATE
ETHYL 3-OXOBUTANOATE
ETHYL 3-OXOBUTANOIC ACID
ETHYL 3-OXOBUTYRATE
ETHYL ACETOACETATE
Ethyl acetyl acetate
ethyl beta-ketobutyrate
FEMA 2415 | [EINECS(EC#)]
205-516-1 | [Molecular Formula]
C6H10O3 | [MDL Number]
MFCD00009199 | [Molecular Weight]
130.14 | [MOL File]
141-97-9.mol |
| Chemical Properties | Back Directory | [Definition]
This compound is a tautomer at room temperature
consisting of about 93% keto form and 7% enol
form. | [Appearance]
Colourless, clear liquid | [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)
| [FEMA ]
2415 | [refractive index ]
n20/D 1.419
| [Fp ]
185 °F
| [storage temp. ]
Store below +30°C. | [solubility ]
116 g/L (20°C) | [form ]
Liquid | [pka]
11(at 25℃) | [color ]
APHA: ≤15 | [Specific Gravity]
1.027～1.035 (20/4℃) | [Odor]
Agreeable, fruity. | [PH]
4.0 (110g/l, H2O, 20℃) | [Relative polarity]
0.577 | [Stability:]
Stable. Incompatible with acids, bases, oxidizing agents, reducing agents, alkali metals. Combustible. | [explosive limit]
1.0-54%(V) | [Odor Type]
fruity | [Water Solubility ]
116 g/L (20 ºC) | [Usage]
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 | [JECFA Number]
595 | [Merck ]
14,3758 | [BRN ]
385838 | [Dielectric constant]
15.0（Ambient） | [InChIKey]
XYIBRDXRRQCHLP-UHFFFAOYSA-N | [LogP]
0.8 at 20℃ | [CAS DataBase Reference]
141-97-9(CAS DataBase Reference) | [NIST Chemistry Reference]
Butanoic acid, 3-oxo-, ethyl ester(141-97-9) | [EPA Substance Registry System]
141-97-9(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36:Irritating to the eyes. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S24/25:Avoid contact with skin and eyes . | [RIDADR ]
UN 1993 | [WGK Germany ]
1
| [RTECS ]
AK5250000
| [Autoignition Temperature]
580 °F | [TSCA ]
Yes | [HazardClass ]
3.2 | [PackingGroup ]
III | [HS Code ]
29183000 | [Safety Profile]
eye 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. | [Hazardous Substances Data]
141-97-9(Hazardous Substances Data) | [Toxicity]
LD50 orally in rats: 3.98 g/kg (Smyth) |
| Hazard Information | Back Directory | [General Description]
A 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. | [Reactivity Profile]
ETHYL ACETOACETATE(141-97-9), 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(141-97-9) (Soriano, D.S. et al. 1988. Journal of Chemical Education 65:637.).1971]. | [Air & Water Reactions]
Flammable. | [Hazard]
Toxic by ingestion and inhalation; irritant
to skin and eyes. | [Health Hazard]
Liquid may cause mild irritation of eyes. | [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. | [Chemical Properties]
Ethyl 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. | [Chemical Properties]
Ethyl acetoacetate has a characteristic ether-like, fruity, pleasant, refreshing odor. | [Occurrence]
Naturally occurring in strawberry, coffee, sherry, passion fruit juice (yellow), babaco fruit (Carica pentagona
Heilborn) and bread. | [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 | [Application]
Ethyl acetoacetate can be used as a potential bio-based diluent for improving the cold flow properties of biodiesel from waste cooking oil[1]. Ethyl acetoacetate reacts with glycosylamines to form ethyl 3-(glycosylamino)crotonate, which is further transformed into ethyl 2-methyl-4-(polyhydroxyalkyl)pyrrole-3-carboxylates under conditions that promote the Amadori rearrangement of glycosylamines. It also reacts with ketohexylamines (D-fructosylamine, L-sorbosylamine) to form ethyl 2-methyl-5-(tetrahydroxybutyl)pyrrole-3-carboxylates[2]. | [Preparation]
Ethyl 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. | [Production Methods]
Ethyl acetoacetate is manufactured through a reaction of
high-purity ethyl acetate with sodium, followed by neutralization
with sulfuric acid. | [Aroma threshold values]
Detection: 520 ppb. Aroma characteristics at 10%: sweet fruity apple, fermented, slightly fusel-like and
rummy, fruity banana with tropical nuances. | [Taste threshold values]
Taste 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 | [Flammability and Explosibility]
Nonflammable | [Chemical Reactivity]
Ethyl 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. | [Chemical Reactivity]
Reactivity 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. | [Synthesis]
Ethyl 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. | [storage]
Store at -20°C | [Purification Methods]
Shake 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.] | [References]
[1] LEICHANG CAO. Ethyl acetoacetate: A potential bio-based diluent for improving the cold flow properties of biodiesel from waste cooking oil[J]. Applied Energy, 2014, 114: Pages 18-21. DOI:10.1016/j.apenergy.2013.09.050.
[2] A.GóMEZ SáNCHEZ; J. V del P. Reaction of glycosylamines with ethyl acetoacetate[J]. Carbohydrate Research, 1966, 1 6: Pages 421-434. DOI:10.1016/S0008-6215(00)81220-3.
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