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Ethyl acetoacetate

CAS No.
141-97-9
Chemical Name:
Ethyl acetoacetate
Synonyms
ETHYL 3-OXOBUTANOATE;ACE;EAA;Ethyl acetoacetate, 99%, pure;ACETOACETIC ESTER;Ethyl acetyl acetate;Acetoacetic acid ethyl;Ethyl acetoacetate(EAA);Ethyl acetoacetate, extra pure;3-OXOBUTANOIC ACID ETHYL ESTER
CBNumber:
CB0301721
Molecular Formula:
C6H10O3
Lewis structure
c6h10o3 lewis structure
Molecular Weight:
130.14
MDL Number:
MFCD00009199
MOL File:
141-97-9.mol
Last updated:2025-09-25 17:15:13
Product description Number Pack Size Price
Ethyl acetoacetate natural, ≥97%, FG W241512 1 unit $60.5
Ethyl acetoacetate natural, ≥97%, FG W241512 1 unit $60.5
Ethyl acetoacetate natural, ≥97%, FG W241512 100g $64.41
Ethyl acetoacetate natural, ≥97%, FG W241512 1kg $213
Ethyl acetoacetate natural, ≥97%, FG W241512 5kg $904
More product size

Ethyl acetoacetate 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 n20/D 1.419
FEMA 2415 | ETHYL ACETOACETATE
Flash point 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℃)
Odor Agreeable, fruity.
PH 4.0 (110g/l, H2O, 20℃)
Relative polarity 0.577
explosive limit 1.0-54%(V)
Odor Type fruity
biological source synthetic
Water Solubility 116 g/L (20 ºC)
JECFA Number 595
Merck 14,3758
BRN 385838
Dielectric constant 15.0(Ambient)
Stability Stable. Incompatible with acids, bases, oxidizing agents, reducing agents, alkali metals. Combustible.
InChIKey XYIBRDXRRQCHLP-UHFFFAOYSA-N
LogP 0.8 at 20℃
Surface tension 31.93mN/m at 298.15K
Substances Added to Food (formerly EAFUS) ETHYL ACETOACETATE
FDA 21 CFR 172.515; 175.300
CAS DataBase Reference 141-97-9(CAS DataBase Reference)
EWG's Food Scores 1
FDA UNII IZP61H3TB1
NIST Chemistry Reference Butanoic acid, 3-oxo-, ethyl ester(141-97-9)
EPA Substance Registry System Ethyl acetoacetate (141-97-9)
UNSPSC Code 85151701
NACRES NA.24

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H227-H319-H303
Precautionary statements  P210e-P280a-P305+P351+P338-P337+P313-P501a-P210-P264-P280-P305+P351+P338+P337+P313-P370+P378-P403+P235-P501
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)
Excepted Quantities Non-Hazardous
NFPA 704
2
1 0

Ethyl acetoacetate price More Price(55)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich W241512 Ethyl acetoacetate natural, ≥97%, FG 141-97-9 1 unit $60.5 2025-07-31 Buy
Sigma-Aldrich W241512 Ethyl acetoacetate natural, ≥97%, FG 141-97-9 1 unit $60.5 2025-07-31 Buy
Sigma-Aldrich W241512 Ethyl acetoacetate natural, ≥97%, FG 141-97-9 100g $64.41 2025-07-31 Buy
Sigma-Aldrich W241512 Ethyl acetoacetate natural, ≥97%, FG 141-97-9 1kg $213 2025-07-31 Buy
Sigma-Aldrich W241512 Ethyl acetoacetate natural, ≥97%, FG 141-97-9 5kg $904 2025-07-31 Buy
Product number Packaging Price Buy
W241512 1 unit $60.5 Buy
W241512 1 unit $60.5 Buy
W241512 100g $64.41 Buy
W241512 1kg $213 Buy
W241512 5kg $904 Buy

Ethyl acetoacetate Chemical Properties,Uses,Production

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 is used as an intermediate in organic synthesis and as a co-promoter for unsaturated polyester resins. It is widely used in the production of dyes, inks, perfumes, plastics and flavoring agents. It is an important starting material for the syntheses of alpha-substituted acetoacetic esters and cyclic compounds like pyrazole, pyrimidine and coumarin derivatives. It acts as an intermediate in the synthesis of vitamins and pharmaceuticals. It finds application as a formaldehyde scavenger.

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.

Definition

ChEBI: Ethyl acetoacetate is an ethyl ester resulting from the formal condensation of the carboxy group of acetoacetic acid with ethanol. It has a role as a flavouring agent, an antibacterial agent and a plant metabolite. It is functionally related to an acetoacetic acid.

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].

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

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.

Air & Water Reactions

Flammable.

Reactivity Profile

Ethyl 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].

Hazard

Toxic by ingestion and inhalation; irritant to skin and eyes.

Health Hazard

Liquid may cause mild irritation of eyes.

Flammability and Explosibility

Non flammable

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.

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.

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.]

Toxics Screening Level

The initial threshold screening level (ITSL) for ethyl acetoacetate is 46 μg/m3 based on an annual averaging time.

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.

674-82-8
64-17-5
141-97-9
Synthesis of Ethyl acetoacetate from Acetyl ketene and Ethanol
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View Lastest Price from Ethyl acetoacetate manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Ethyl acetoacetate pictures 2025-10-15 Ethyl acetoacetate
141-97-9
0.99 RongNa Biotechnology Co.,Ltd
Ethyl acetoacetate pictures 2025-10-15 Ethyl acetoacetate
141-97-9
US $0.00 / kg 1kg 98%min 10 tons WUHAN FORTUNA CHEMICAL CO., LTD
Ethyl acetoacetate pictures 2025-10-11 Ethyl acetoacetate
141-97-9
US $0.00-0.00 / mg 5mg 95%+ 1000mg Guangzhou Tosun Pharmaceutical Ltd
Ethyl acetoacetate, 99%, pure Ethyl acetoacetate, extra pure Acetoacetic acid ethyl Ethyl acetoacetate,Acetoacetic ester Ethyl acetoacetate, synthesis grade Ethyl acetoacetate,99+%,extra pure Ethyl acetoacetate >=99.0% 2-ethyl-3-oxobutanoate Ethyl acetoacetate, extra pure, 99+% 100GR Ethyl acetoacetate, pure, 99% 1LT Ethyl acetoacetate, pure, 99% 2.5LT FEMA 2415 LABOTEST-BB LT01690211 EAA ETHYL 3-OXOBUTANATE ETHYL 3-OXOBUTANOATE ETHYL 3-OXOBUTANOIC ACID ETHYL 3-OXOBUTYRATE ETHYL 3-KETOBUTANOATE ethyl beta-ketobutyrate ETHYL ACETOACETATE Ethyl acetyl acetate DIACETIC ETHER activeacetylacetate Butanoicacid,3-oxo-,ethylester diaceticester EAA en Ethylacetacetat ethylacetylacetonate Ethylester kyseliny acetoctove ethylesterkyselinyacetoctove thyl acetyl acetate ACE, Acetoacetic ester Acetoacetic ester, EAA Ethyl acetoacetate(N/A) EAA)Ethyl acetoace Ethyl acetoacetate puriss. p.a., >=99.0% (GC) Acetoacetic Acid Ethyl Ester Ethyl 3-Oxobutyrate 3-Oxobutyric Acid Ethyl Ester Natural ethyl acetoacetate ETHYL ACETOACETATE, 99%ETHYL ACETOACETATE, 99%ETHYL ACETOACETATE, 99%ETHYL ACETOACETATE, 99% 3-OXOBUTANOIC ACID ETHYL ESTER 3-OXOBUTYRIC ACID ETHYL ESTER 3-KETOBUTANOIC ACID ETHYL ESTER ACETOACETIC ESTER ACETOACETIC ESTER (ETHYL) ACETOACETIC ETHER ACETOACETIC ACID ETHYL ESTER ACE AKOS BBS-00004335 1-ethoxybutane-1,3-dione 3-oxo-butanoicaciethylester acetoacetated’ethyle Acetoctan ethylnaty acetoctanethylnaty Active acetylacetate Ethyl acetoacetate-1-13C Acetessigsureethylester ETHYLACETOACETAT (ACETESSIGESTER)