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Product Name: |
Natural ethyl acetoacetate |
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CAS: |
141-97-9 |
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MF: |
C6H10O3 |
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MW: |
130.14 |
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EINECS: |
205-516-1 |
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Mol File: |
141-97-9.mol |
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|
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Melting point |
−43 °C(lit.) |
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Boiling point |
181 °C(lit.) |
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density |
1.029 g/mL at 20 °C(lit.) |
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vapor density |
4.48 (vs air) |
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vapor pressure |
1 mm Hg ( 28.5 °C) |
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refractive index |
n20/D 1.419 |
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FEMA |
2415 | ETHYL ACETOACETATE |
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Fp |
185 °F |
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storage temp. |
Store below +30°C. |
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solubility |
116 g/L (20°C) |
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pka |
11(at 25℃) |
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form |
Liquid |
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color |
APHA: ≤15 |
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Specific Gravity |
1.027～1.035 (20/4℃) |
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Relative polarity |
0.577 |
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Odor |
Agreeable, fruity. |
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PH |
4.0 (110g/l, H2O, 20℃) |
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explosive limit |
1.0-54%(V) |
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Water Solubility |
116 g/L (20 ºC) |
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JECFA Number |
595 |
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Merck |
14,3758 |
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BRN |
385838 |
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Stability: |
Stable. Incompatible with acids, bases, oxidizing agents, reducing agents, alkali metals. Combustible. |
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InChIKey |
XYIBRDXRRQCHLP-UHFFFAOYSA-N |
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CAS DataBase Reference |
141-97-9(CAS DataBase Reference) |
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NIST Chemistry Reference |
Butanoic acid, 3-oxo-, ethyl ester(141-97-9) |
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EPA Substance Registry System |
Ethyl acetoacetate (141-97-9) |
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Hazard Codes |
Xi |
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Risk Statements |
36 |
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Safety Statements |
26-24/25 |
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RIDADR |
UN 1993 |
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WGK Germany |
1 |
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RTECS |
AK5250000 |
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Autoignition Temperature |
580 °F |
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TSCA |
Yes |
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HazardClass |
3.2 |
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PackingGroup |
III |
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HS Code |
29183000 |
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Hazardous Substances Data |
141-97-9(Hazardous Substances Data) |
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Toxicity |
LD50 orally in rats: 3.98 g/kg (Smyth) |
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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. |
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Chemical Properties |
Ethyl acetoacetate has a characteristic ether-like, fruity, pleasant, refreshing odor. |
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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. |
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Occurrence |
Naturally occurring in strawberry, coffee, sherry, passion fruit juice (yellow), babaco fruit (Carica pentagona Heilborn) and bread. |
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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 |
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Definition |
This compound is a tautomer at room temperature consisting of about 93% keto form and 7% enol form. |
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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. |
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Chemical 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. |
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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.] |
