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Ethyl acetoacetate

Product Name
Ethyl acetoacetate
CAS No.
141-97-9
Chemical Name
Ethyl acetoacetate
Synonyms
EAA;ACE;EAA en;FEMA 2415;diaceticester;DIACETIC ETHER;Ethylacetacetat;ACETOACETIC ESTER;ACETOACETIC ETHER;AKOS BBS-00004335
CBNumber
CB0301721
Molecular Formula
C6H10O3
Formula Weight
130.14
MOL File
141-97-9.mol
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Ethyl acetoacetate Property

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℃)
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)
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Safety

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)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H227Combustible liquid

H303May be harmfulif swallowed

H319Causes serious eye irritation

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P337+P313IF eye irritation persists: Get medical advice/attention.

P370+P378In case of fire: Use … for extinction.

P403+P235Store in a well-ventilated place. Keep cool.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
W241504
Product name
Ethylacetoacetate
Purity
≥99%,FCC,FG
Packaging
1 SAMPLE-K
Price
$50
Updated
2021/12/16
Sigma-Aldrich
Product number
W241512
Product name
Ethylacetoacetate
Purity
natural,≥97%,FG
Packaging
1 SAMPLE-K
Price
$50
Updated
2021/12/16
Sigma-Aldrich
Product number
8.09622
Product name
Ethyl acetoacetate
Purity
for synthesis
Packaging
100 mL
Price
$31.36
Updated
2021/12/16
Sigma-Aldrich
Product number
00410
Product name
Ethyl acetoacetate
Purity
puriss. p.a., ≥99.0% (GC)
Packaging
100ml
Price
$39.2
Updated
2021/12/16
Sigma-Aldrich
Product number
W241512
Product name
Ethyl acetoacetate
Purity
natural, ≥97%, FG
Packaging
100 g
Price
$70
Updated
2021/12/16
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Ethyl acetoacetate Chemical Properties,Usage,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 (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

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.

Definition

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

Production Methods

Ethyl acetoacetate is manufactured through a reaction of high-purity ethyl acetate with sodium, followed by neutralization with sulfuric acid.

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.

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.

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.

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.

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.]

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Ethyl acetoacetate Suppliers

Shanghai Aladdin Bio-Chem Technology Co.,LTD
Tel
400-62063333-1
Fax
021-50323701
Email
market@aladdin-e.com
Country
China
ProdList
24980
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65
Shanghai Rolead Chemical Technology Co., Ltd.
Tel
021-69992230- ;021-69992220-
Fax
021-69992237
Email
roleadchem@163.com;roleadchem@163.com
Country
China
ProdList
3335
Advantage
50
Jinan Century Tongda Chemical Co., Ltd.
Tel
0531-58051019- ;0531-58051019-
Fax
0531-85917596
Email
3350933950@qq.com;3350933950@qq.com
Country
China
ProdList
280
Advantage
58
Guangzhou Hongcheng Biotechnology Co., Ltd
Tel
Email
chenshun157@163.com;
Country
China
ProdList
474
Advantage
58
Nanjing Apicci Pharmaceutical Technology Co., Ltd.
Tel
;
Fax
QQ2853590738
Email
2853590738@qq.com;2853579352@qq.com
Country
China
ProdList
406
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58
Shandong Jinyueyuan New Material Co. Ltd
Tel
;
Email
3404852510@qq.com;3404852510@qq.com
Country
China
ProdList
190
Advantage
58
J & K SCIENTIFIC LTD.
Tel
010-82848833- ;010-82848833-
Fax
86-10-82849933
Email
jkinfo@jkchemical.com;market6@jkchemical.com
Country
China
ProdList
96815
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76
Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
+86-021-61259100
Fax
86-21-61259102
Email
int02@meryer.com
Country
China
ProdList
40264
Advantage
62
3B Pharmachem (Wuhan) International Co.,Ltd.
Tel
821-50328103-801
Fax
86-21-50328109
Email
3bsc@sina.com
Country
China
ProdList
15877
Advantage
69
Alfa Aesar
Tel
400-610-6006; 021-67582000
Fax
021-67582001/03/05
Email
saleschina@alfa-asia.com
Country
China
ProdList
30159
Advantage
84
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View Lastest Price from Ethyl acetoacetate manufacturers

Wuhan Mulei New Material Technology Co. Ltd
Product
Ethyl acetoacetate 141-97-9
Price
US $0.00/Kg/Drum
Min. Order
1KG
Purity
99.9%
Supply Ability
100000kg per month
Release date
2021-04-03
XINGTAI XINGJIU NEW MATERIAL TECHNOLOGY CO., LTD
Product
Ethyl acetoacetate 141-97-9
Price
US $15.00/KG
Min. Order
1KG
Purity
99.9%
Supply Ability
500MT/month
Release date
2021-12-20
Guangzhou Sunton Biotechnology Co., Ltd.
Product
Ethyl acetoacetate 141-97-9
Price
US $48.00-40.00/KG
Min. Order
1公斤
Purity
99%
Supply Ability
2tons
Release date
2021-06-04

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