Ethyl acetoacetate
- Iupac Name：ethyl 3-oxobutanoate
- CAS No.: 141-97-9
- Molecular Weight：130.1418
- Modify Date.: 2022-11-11 00:37
- Introduction: 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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1. Names and Identifiers
- 1.1 Name
- Ethyl acetoacetate
- 1.2 Synonyms
2-ethyl-3-oxobutanoate 3-Oxobutanoic acid, ethyl ester 3-Oxobutyric acid ethyl ester Acetoacetic acid ethyl acetoacetic acid ethyl ester ACETOACETIC ESTER Butanoic acid, 3-oxo-, ethyl ester EINECS 205-516-1 Ethyl 3-oxobutyrate ethyl 3-oxo-butyrate Ethyl acetoacetate, extra pure Ethyl acetoacetate, synthesis grade Ethyl acetoacetate,Acetoacetic ester ETHYL ACETYLACETATE ethylacetoacetate MFCD00009199
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- 1.3 CAS No.
- 141-97-9
- 1.4 CID
- 8868
- 1.5 EINECS(EC#)
- 205-516-1
- 1.6 Molecular Formula
- C6H10O3 (isomer)
- 1.7 Inchi
- InChI=1S/C6H10O3/c1-3-9-6(8)4-5(2)7/h3-4H2,1-2H3
- 1.8 InChIkey
- XYIBRDXRRQCHLP-UHFFFAOYSA-N
- 1.9 Canonical Smiles
- CCOC(=O)CC(=O)C
- 1.10 Isomers Smiles
- CCOC(=O)CC(=O)C
2. Properties
- 2.1 Density
- 1.021
- 2.1 Melting point
- -45℃
- 2.1 Boiling point
- 180℃
- 2.1 Refractive index
- 1.418-1.42
- 2.1 Flash Point
- 70℃
- 2.2 Precise Quality
- 130.06300
- 2.2 PSA
- 43.37000
- 2.2 logP
- 0.52860
- 2.2 Solubility
- 116 g/L (20 °C)
- 2.3 VaporDensity
- 4.48 (vs air)
- 2.4 Appearance
- Colourless liquid
- 2.5 Storage
- Ambient temperatures.
- 2.6 Autoignition Temperature
- 563 °F (USCG, 1999)
- 2.7 Chemical Properties
- Ethyl acetoacetate has a characteristic ether-like, fruity, pleasant, refreshing odor.
- 2.8 Color/Form
- COLORLESS LIQUID
- 2.9 Odor
- PLEASANT GREEN, FRUITY, RUM ODOR
- 2.10 PH
- 4.0 (110g/l, H2O, 20℃)
- 2.11 pKa
- 11(at 25℃)
- 2.12 Water Solubility
- 116 g/L (20 oC)
- 2.13 Spectral Properties
- MAX ABSORPTION (ALCOHOL): 248 NM (LOG E= 3.2); INDEX OF REFRACTION: 1.4194 AT 20 DEG C/D; SADTLER REFERENCE NUMBER: 101 (IR, PRISM)
MASS: 265 (National Bureau of Standards EPA-NIH Mass Spectra Data Base, NSRDS-NBS-63)
IR: 14440 (Sadtler Research Laboratories Prism Collection)
- 2.14 Stability
- Stable. Incompatible with acids, bases, oxidizing agents, reducing agents, alkali metals. Combustible.
- 2.15 StorageTemp
- Store below +30°C.
3. Use and Manufacturing
- 3.1 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.
- 3.2 Definition
- This compound is a tautomer at room temperatureconsisting of about 93% keto form and 7% enolform.
- 3.3 Produe Method
- Ethyl acetoacetate is manufactured through a reaction ofhigh-purity ethyl acetate with sodium, followed by neutralizationwith sulfuric acid.
- 3.4 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.] Ethyl acetoacetate Preparation Products And Raw materials Raw materials
- 3.5 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
4. Safety and Handling
- 4.1 Hazard Codes
- Xi
- 4.1 Risk Statements
- R36
- 4.1 Safety Statements
- S24/25
- 4.1 Exposure Standards and Regulations
- FDA 121.1164.
FDA 172.515. FLAVOR USEFUL IN STRAWBERRY, FRUIT FLAVORS.
- 4.2 Packing Group
- III
- 4.2 Octanol/Water Partition Coefficient
- log Kow = 0.25
- 4.3 Hazard Class
- 3.2
- 4.3 RIDADR
- UN 1993
- 4.3 Fire Fighting Procedures
- USE ALCOHOL FOAM, CARBON DIOXIDE, DRY CHEMICAL.
- 4.4 FirePotential
- MODERATE WHEN EXPOSED TO HEAT OR FLAME.
- 4.5 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 2,2,2tris(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.
- 4.6 Formulations/Preparations
- GRADES: TECHNICAL; 98%.
- 4.7 WGK Germany
- 1
- 4.7 RTECS
- AK5250000
- 4.7 Protective Equipment and Clothing
- IRRITANT TO EYES.
- 4.8 Report
-
Reported in EPA TSCA Inventory.
- 4.9 Skin, Eye, and Respiratory Irritations
- IRRITANT TO EYES.
- 4.10 Safety
-
Safety Information of Ethyl acetoacetate (CAS NO.141-97-9):
Hazard Codes:?
Xi
Risk Statements: 36
R36: Irritating to eyes.
Safety Statements: 26-24/25?
S24/25: Avoid contact with skin and eyes.?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
RIDADR: UN 1993
WGK Germany: 1
RTECS: AK5250000
HazardClass: 3.2
PackingGroup: III
Moderately toxic by ingestion. A skin and eye irritant. Combustible liquid when exposed to heat or flame; can react with oxidizing materials. Explosive reaction when heated with Zn + tribromoneopentyl alcohol or 2,2,2-tris(bromomethyl)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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- 4.11 Specification
-
General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. Will burn if involved in a fire. Combustible liquid.
Extinguishing Media: Use water spray to cool fire-exposed containers. Use water spray, dry chemical, carbon dioxide, or chemical foam.?
Handling: Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage: Keep away from sources of ignition. Store in a cool, dry place. Store in a tightly closed container.
- 4.12 Toxicity
-
| Organism |
Test Type |
Route |
Reported Dose (Normalized Dose) |
Effect |
Source |
| mouse |
LD50 |
oral |
5105mg/kg (5105mg/kg) |
? |
Journal of Pharmaceutical Sciences. Vol. 60, Pg. 1810, 1971. |
| rabbit |
LD |
skin |
> 20mL/kg (20mL/kg) |
? |
Union Carbide Data Sheet. Vol. 3/12/1969, |
| rat |
LD50 |
oral |
3980mg/kg (3980mg/kg) |
? |
Journal of Industrial Hygiene and Toxicology. Vol. 31, Pg. 60, 1949. |
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5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
Not classified.
2.2 GHS label elements, including precautionary statements
| Pictogram(s) | No symbol. |
| Signal word | No signal word. |
| Hazard statement(s) | none |
| Precautionary statement(s) | |
| Prevention | none |
| Response | none |
| Storage | none |
| Disposal | none |
2.3 Other hazards which do not result in classification
none
7. Synthesis Route
141-97-9Total: 178 Synthesis Route
9. Other Information
- 9.0 Merck
- 14,3758
- 9.1 BRN
- 385838
- 9.2 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.
- 9.3 Chemical Properties
- Ethyl acetoacetate has a characteristic ether-like, fruity, pleasant, refreshing odor.
- 9.4 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.
- 9.5 Occurrence
- Naturally occurring in strawberry, coffee, sherry, passion fruit juice (yellow), babaco fruit (Carica pentagona Heilborn) and bread.
- 9.6 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
- 9.7 Definition
- This compound is a tautomer at room temperature consisting of about 93% keto form and 7% enol form.
- 9.8 Production Methods
- Ethyl acetoacetate is manufactured through a reaction of high-purity ethyl acetate with sodium, followed by neutralization with sulfuric acid.
- 9.9 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.
- 9.10 Aroma threshold values
- Detection: 520 ppb. Aroma characteristics at 10%: sweet fruity apple, fermented, slightly fusel-like and rummy, fruity banana with tropical nuances.
- 9.11 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
- 9.12 Synthesis Reference(s)
- The Journal of Organic Chemistry, 58, p. 793, 1993 DOI: 10.1021/jo00055a046
- 9.13 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.
- 9.14 Air & Water Reactions
- Flammable.
- 9.15 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].
- 9.16 Hazard
- Toxic by ingestion and inhalation; irritant to skin and eyes.
- 9.17 Health Hazard
- Liquid may cause mild irritation of eyes.
- 9.18 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.
- 9.19 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.
- 9.20 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.
- 9.21 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.
- 9.22 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.]
- 9.23 Usage
- 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.
10. Computational chemical data
- Molecular Weight: 130.1418g/mol
- Molecular Formula: C6H10O3
- Compound Is Canonicalized: True
- XLogP3-AA: null
- Exact Mass: 130.062994177
- Monoisotopic Mass: 130.062994177
- Complexity: 118
- Rotatable Bond Count: 4
- Hydrogen Bond Donor Count: 0
- Hydrogen Bond Acceptor Count: 3
- Topological Polar Surface Area: 43.4
- Heavy Atom Count: 9
- Defined Atom Stereocenter Count: 0
- Undefined Atom Stereocenter Count: 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Isotope Atom Count: 0
- Covalently-Bonded Unit Count: 1
- CACTVS Substructure Key Fingerprint: AAADccBgMAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAGgAAAAAACASggAICCAAABAAIAICQCAAAAAAAAAAAAAEAAAAAABQIAAACAAAEIAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
11. Question & Answer
-
Ethyl Acetoacetate (EA) is a commonly used organic solvent with the chemical formula C4H8O2 and a molecular weight of 88.11 g/mol. Its structural formula is CH3COOCH2CH3. Ethyl Acetoacetate is primari..
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Introduction Ethyl acetoacetate is an important organic synthesis material used in the pharmaceutical industry for the synthesis of amino pyridine, vitamin B, and other compounds. It is also used in t..
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Different from liquids with irritating odors, this component, Ethyl acetoacetate, has a pleasant aroma, so it is not particularly pungent and is included in many pharmaceutical intermediates. Its chem..
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Are you sure that the proposition of the question is correct? The negative charge of acetoacetic enolate is spread over FIVE centres… Bing Image Trending The negative charge of methyl sodium is CONFI..
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