Natural Ethyl Acetoacetate

Product Name:

Natural ethyl acetoacetate

CAS:

141-97-9

MF:

C6H10O3

MW:

130.14

EINECS:

205-516-1

Mol File:

141-97-9.mol

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 

n20/D 1.419

FEMA 

2415 | ETHYL ACETOACETATE

Fp 

185 °F

storage temp. 

Store below +30°C.

solubility 

116 g/L (20°C)

pka

11(at 25℃)

form 

Liquid

color 

APHA: ≤15

Specific Gravity

1.027～1.035 (20/4℃)

Relative polarity

0.577

Odor

Agreeable, fruity.

PH

4.0 (110g/l, H2O, 20℃)

explosive limit

1.0-54%(V)

Water Solubility 

116 g/L (20 ºC)

JECFA Number

595

Merck 

14,3758

BRN 

385838

Stability:

Stable. Incompatible with acids, bases, oxidizing agents, reducing agents, alkali metals. Combustible.

InChIKey

XYIBRDXRRQCHLP-UHFFFAOYSA-N

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

Ethyl acetoacetate (141-97-9)

Hazard Codes 

Xi

Risk Statements 

36

Safety Statements 

26-24/25

RIDADR 

UN 1993

WGK Germany 

1

RTECS 

AK5250000

Autoignition Temperature

580 °F

TSCA 

Yes

HazardClass 

3.2

PackingGroup 

III

HS Code 

29183000

Hazardous Substances Data

141-97-9(Hazardous Substances Data)

Toxicity

LD50 orally in rats: 3.98 g/kg (Smyth)

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 acetoacetate has a characteristic ether-like, fruity, pleasant, refreshing odor.

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.

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

Definition

This compound is a tautomer at room temperature consisting of about 93% keto form and 7% enol form.

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.

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.

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.]