Acetoacetic acid allyl ester is a versatile organic compound with a range of applications in chemical synthesis, polymer production, and occasionally in the flavor and fragrance industry.
As a colorless liquid with a potent fragrance, Acetoacetic acid allyl ester effortlessly dissolves in various organic solvents, making it a valuable asset in the synthesis of numerous compounds.
The reaction involving allyl alcohol and acetic anhydride in the presence of a catalyst results in Acetoacetic acid allyl ester as one of the primary products, along with acetic acid.
CAS Number: 1118-84-9
EC Number: 214-269-9
Molecular Formula: C7H10O3
Molar Mass: 142.16 g/mol
Synonyms: Allyl acetoacetate, 1118-84-9, Allyl 3-oxobutanoate, Allylacetoacetate, (2-Propenyl) 3-oxobutanoate, Allyl acetylacetate, Acetoacetic acid, allyl ester, Butanoic acid, 3-oxo-, 2-propenyl ester, prop-2-en-1-yl 3-oxobutanoate, prop-2-enyl 3-oxobutanoate, Acetoacetic Acid Allyl Ester, (2-Propenyl)3-oxobutanoate, 8HX066J62P, NSC-24280, 2-propenyl acetoacetate, UNII-8HX066J62P, AI3-04977, allyl aceto-acetate, EINECS 214-269-9, Allyl 3-oxobutanoate #, Allyl acetoacetate, 97%, Allyl acetoacetate, 98%, EC 214-269-9, SCHEMBL9513, Acetylacetic acid, allyl ester, 3-oxo-butyric acid allyl ester, DTXSID40149740, BCP12037, NSC24280, BBL011433, MFCD00009811, NSC 24280, STL146541, AKOS000120505, CS-W018294, VS-02949, DB-003129, NS00001809, EN300-20951, E75749, J-002655, J-519551, Q27270546, F0001-0255, Allyl acetoacetate, Prop-2-en-1-yl 3-oxobutanoate, Butanoic acid, 3-oxo-, 2-propen-1-yl ester, 1118-84-9, EINECS 214-269-9, Butanoic acid, 3-oxo-, 2-propen-1-yl ester, Acetoacetic acid, allyl ester, Butanoic acid, 3-oxo-, 2-propenyl ester, Allyl acetoacetate, Allyl acetylacetate, Allyl 3-oxobutanoate, NSC 24280, 3-Oxo-butyric acid allyl ester, Allyl acetoacetate, Acetoacetic acid allyl ester, Allyl acetoacetate, allyl 3-oxobutanoate, allyl acetylacetate, acetoacetic acid, allyl ester, butanoic acid, 3-oxo-, 2-propenyl ester, prop-2-en-1-yl 3-oxobutanoate, acetoacetic acid allyl ester, 2-propenyl 3-oxobutanoate, ac-allyl, unii-8hx066j62p, prop-2-en-1-yl 3-oxobutanoate, allyl acetylacetate, 3-oxo-2-propenyl butanoic acid ester, Butanoic acid, 3-oxo-, 2-propenyl ester, [ChemIDplus] Allyl 3-oxobutanoate, Allyl acetoacetate, allyl 3-oxobutanoate, allyl acetylacetate, acetoacetic acid, allyl ester, butanoic acid, 3-oxo-, 2-propenyl ester, prop-2-en-1-yl 3-oxobutanoate, acetoacetic acid allyl ester, 2-propenyl 3-oxobutanoate, ac-allyl, unii-8hx066j62p
Acetoacetic acid allyl ester is an organic compound that is the simplest member of the acetic acid esters.
Acetoacetic acid allyl ester can be synthesized by reacting allyl alcohol with hydrochloric acid and a particle.
Acetoacetic acid allyl ester is a clear colorless liquid.
Acetoacetic acid allyl ester has been shown to have cytotoxic effects on cardiac tissues, as well as certain reactive properties, which may be due to Acetoacetic acid allyl ester's ability to form cross-links with proteins.
Acetoacetic acid allyl ester is registered under the REACH Regulation but is not currently being manufactured in and / or imported to the European Economic Area.
Acetoacetic acid allyl ester is an adhesion promoter.
Acetoacetic acid allyl ester is available in colorless to pale yellow colored liquid form.
Acetoacetic acid allyl ester is recommended for coatings.
Acetoacetic acid allyl ester holds significant importance as an organic compound widely utilized in chemical synthesis and scientific exploration.
As a colorless liquid with a potent fragrance, Acetoacetic acid allyl ester effortlessly dissolves in various organic solvents.
Acetoacetic acid allyl ester's versatility in the synthesis of numerous compounds makes Acetoacetic acid allyl ester a valuable asset.
Moreover, Acetoacetic acid allyl ester plays a role in the creation of polymers, dyes, and catalysts.
Fascinatingly, Acetoacetic acid allyl ester finds application in the synthesis of essential biochemicals, such as vitamins, hormones, and enzymes.
In scientific research, particularly in organic synthesis, Acetoacetic acid allyl ester is highly regarded and employed.
The reaction involving allyl alcohol and acetic anhydride in the presence of a catalyst results in Acetoacetic acid allyl ester as one of the primary products, along with acetic acid.
For this reaction, an inert atmosphere and a temperature of around 100°C are typically maintained.
The outcome of this process serves as a pivotal intermediate for a diverse range of compounds, making Acetoacetic acid allyl ester an indispensable component in various scientific and industrial endeavors.
Acetoacetic acid allyl ester is registered under the REACH Regulation but is not currently being manufactured in and / or imported to the European Economic Area.
Acetoacetic acid allyl ester is used in formulation or re-packing.
Acetoacetic acid allyl ester is an adhesion promoter.
Acetoacetic acid allyl ester is available in colorless to pale yellow colored liquid form.
Acetoacetic acid allyl ester is recommended for coatings.
Acetoacetic acid allyl ester is an organic compound that is the simplest member of the acetic acid esters.
Acetoacetic acid allyl ester can be synthesized by reacting allyl alcohol with hydrochloric acid and a particle.
Acetoacetic acid allyl ester has been shown to have cytotoxic effects on cardiac tissues, as well as certain reactive properties, which may be due to Acetoacetic acid allyl ester's ability to form cross-links with proteins.
Acetoacetic acid allyl ester is also used as a cross-linking agent for polyvinyl chloride plastics.
Acetoacetic acid allyl ester is an organic ester with the chemical formula C7H10O3.
Acetoacetic acid allyl ester is a colorless to light yellow liquid characterized by its pleasant odor.
Acetoacetic acid allyl ester is used primarily as a chemical intermediate in organic synthesis, where Acetoacetic acid allyl ester serves as a building block for the production of a variety of complex molecules, including pharmaceuticals, agrochemicals, and specialty polymers.
Acetoacetic acid allyl ester is a versatile organic compound with a range of applications in chemical synthesis, polymer production, and occasionally in the flavor and fragrance industry.
Acetoacetic acid allyl ester's reactivity and ability to participate in various chemical reactions make it a valuable intermediate in the production of numerous commercially important chemicals.
Uses of Acetoacetic Acid Allyl Ester:
Acetoacetic acid allyl ester is also used as a cross-linking agent for polyvinyl chloride plastics.
Acetoacetic acid allyl ester is used in the formulation of pharmaceuticals and as an intermediate for fine chemicals.
Acetoacetic acid allyl ester is used in formulation or re-packing.
Release to the environment of Acetoacetic acid allyl ester can occur from industrial use: formulation of mixtures.
Moreover, Acetoacetic acid allyl ester plays a role in the creation of polymers, dyes, and catalysts.
Fascinatingly, Acetoacetic acid allyl ester finds application in the synthesis of essential biochemicals, such as vitamins, hormones, and enzymes.
In scientific research, particularly in organic synthesis, Acetoacetic acid allyl ester is highly regarded and employed.
The reaction involving allyl alcohol and acetic anhydride in the presence of a catalyst results in Acetoacetic acid allyl ester as one of the primary products, along with acetic acid.
For this reaction, an inert atmosphere and a temperature of around 100°C are typically maintained.
The outcome of this process serves as a pivotal intermediate for a diverse range of compounds, making Acetoacetic acid allyl ester an indispensable component in various scientific and industrial endeavors.
Applications of Acetoacetic Acid Allyl Ester:
Chemical Synthesis:
Acetoacetic acid allyl ester is commonly used as an intermediate in the synthesis of more complex organic compounds.
Acetoacetic acid allyl ester's reactive ester and ketone groups allow for a variety of chemical reactions, making it valuable in the production of pharmaceuticals and agrochemicals.
Polymer Production:
Acetoacetic acid allyl ester acts as a monomer or comonomer in the creation of specialized polymers and copolymers, contributing properties such as flexibility, durability, and chemical resistance.
Flavor and Fragrance Industry:
Due to its pleasant odor, Acetoacetic acid allyl ester is sometimes used in the formulation of flavors and fragrances, although this is less common than its use in industrial chemical synthesis.
Production of Acetoacetic Acid Allyl Ester:
The production of Acetoacetic acid allyl ester involves the esterification of acetoacetic acid with allyl alcohol.
This process typically requires an acid catalyst to facilitate the reaction. Here is an overview of the general production method:
Materials:
Acetoacetic Acid (C4H6O3)
Allyl Alcohol (C3H6O)
Acid Catalyst (such as sulfuric acid or p-toluenesulfonic acid)
Solvent (optional, often an organic solvent like toluene or ethanol to help dissolve reactants)
Production Process:
Preparation:
Measure and mix the acetoacetic acid and allyl alcohol in the desired molar ratio.
Typically, a slight excess of allyl alcohol is used to drive the reaction to completion.
Catalysis:
Add a small amount of an acid catalyst to the reaction mixture.
The catalyst helps to accelerate the esterification process.
Reaction:
Heat the reaction mixture to a temperature typically between 60-100°C.
Maintain this temperature to facilitate the esterification reaction.
The reaction proceeds as follows:
CH3COCH2COOH+CH2=CHCH2OH→CH3COCH2COOCH2CH=CH2+H2O
The acetoacetic acid reacts with allyl alcohol to form Acetoacetic acid allyl ester and water.
Removal of Water:
The presence of water can drive the reaction equilibrium back to the reactants.
To improve yield, water is typically removed from the reaction mixture as Acetoacetic acid allyl ester forms.
This can be done using azeotropic distillation with a solvent like toluene, which forms an azeotrope with water and can be easily separated.
Purification:
After the reaction is complete, the mixture is cooled.
The crude product is then subjected to purification processes such as distillation under reduced pressure to separate Acetoacetic acid allyl ester from unreacted starting materials and by-products.
Alternatively, Acetoacetic acid allyl ester can be washed with water and dried over anhydrous sodium sulfate or other drying agents to remove any remaining water.
Final Product:
The purified Acetoacetic acid allyl ester is collected as a colorless to light yellow liquid, ready for use in various chemical synthesis applications.
Handling And Storage of Acetoacetic Acid Allyl Ester:
Precautions for safe handling:
Advice on protection against fire and explosion:
Take precautionary measures against static discharge.
Hygiene measures:
Immediately change contaminated clothing.
Apply preventive skin protection.
Wash hands and face after working with substance.
Conditions for safe storage, including any incompatibilities:
Storage conditions:
Protected from light.
Tightly closed.
Keep in a well-ventilated place.
Keep locked up or in an area accessible only to qualified or authorized persons.
Stability And Reactivity of Acetoacetic Acid Allyl Ester:
Chemical stability:
Acetoacetic acid allyl ester is chemically stable under standard ambient conditions (room temperature).
Incompatible materials:
No data available
First Aid Measures of Acetoacetic Acid Allyl Ester:
General advice:
First aiders need to protect themselves.
Show this material safety data sheet to the doctor in attendance.
If inhaled:
After inhalation:
Fresh air.
In case of skin contact:
Take off immediately all contaminated clothing.
Rinse skin with water/ shower.
Call a physician immediately.
In case of eye contact:
After eye contact:
Rinse out with plenty of water.
Remove contact lenses.
If swallowed:
Give water to drink (two glasses at most).
Seek medical advice immediately.
Indication of any immediate medical attention and special treatment needed:
No data available
Fire Fighting Measures of Acetoacetic Acid Allyl Ester:
Suitable extinguishing media:
Water
Foam
Carbon dioxide (CO2)
Dry powder
Unsuitable extinguishing media:
For Acetoacetic acid allyl ester no limitations of extinguishing agents are given.
Further information:
Remove container from danger zone and cool with water.
Prevent fire extinguishing water from contaminating surface water or the ground water system.
Accidental Release Measures of Acetoacetic Acid Allyl Ester:
Environmental precautions:
Do not let product enter drains.
Methods and materials for containment and cleaning up:
Cover drains.
Collect, bind, and pump off spills.
Observe possible material restrictions.
Take up carefully with liquid-absorbent material.
Dispose of properly.
Clean up affected area.
Exposure Controls/Personal Protection of Acetoacetic Acid Allyl Ester:
Personal protective equipment:
Eye/face protection:
Use equipment for eye protection.
Safety glasses
Skin protection:
Full contact:
Material: butyl-rubber
Minimum layer thickness: 0,7 mm
Break through time: 480 min
Splash contact:
Material: Chloroprene
Minimum layer thickness: 0,65 mm
Break through time: 120 min
Body Protection:
protective clothing
Respiratory protection:
Recommended Filter type: Filter A (acc. to DIN 3181)
Control of environmental exposure:
Do not let product enter drains.
Identifiers of Acetoacetic Acid Allyl Ester:
CAS number: 1118-84-9
EC number: 214-269-9
Hill Formula: C₇H₁₀O₃
Chemical formula: CH₃COCH₂COOCH₂CH=CH₂
Molar Mass: 142.16 g/mol
HS Code: 2918 30 00
MDL Number: MFCD00009811
CAS: 1118-84-9
Molecular Weight (g/mol): 142.154
InChI Key: AXLMPTNTPOWPLT-UHFFFAOYSA-N
PubChem CID: 70701
SMILES: CC(=O)CC(=O)OCC=C
UN Number: 2810
InChI Key: AXLMPTNTPOWPLT-UHFFFAOYSA-N
IUPAC Name: prop-2-enyl 3-oxobutanoate
PubChem CID: 70701
Percent Purity: ≥95.0% (GC)
SMILES: CC(=O)CC(=O)OCC=C
Molecular Weight (g/mol): 142.154
CAS number: 1118-84-9
EC number: 214-269-9
Hill Formula: C₇H₁₀O₃
Chemical formula: CH₃COCH₂COOCH₂CH=CH₂
Molar Mass: 142.16 g/mol
Properties of Acetoacetic Acid Allyl Ester:
Solubility: 48 g/l (20 °C)
Molar Mass: 142.15 g/mol
Boiling Point: 87 - 91 °C (13 hPa)
Vapor Pressure: 0.2 hPa (20 °C)
Flash Point: 67 °C
Refractive Index: 1.438 (25 °C, 589 nm)
Explosion Limit: 1.15 %(V)
Density: 1.038 g/cm3 (20 °C)
pH: 3.7 (48 g/l, H2O, 20 °C)
Ignition Point: 300 °C
Chemical Name or Material: Acetoacetic acid allyl ester
Melting Point: -85°C
Boiling Point: 195°C
Formula Weight: 142.15
Physical Form: Liquid
Density: 1.0±0.1 g/cm3
Boiling Point: 192.0±15.0 °C at 760 mmHg
Melting Point: -70 °C
Molecular Formula: C7H10O3
Molecular Weight: 142.152
Flash Point: 75.6±0.0 °C
Exact Mass: 142.062988
PSA: 43.37000
LogP: 1.07
Vapour Pressure: 0.5±0.4 mmHg at 25°C
Index of Refraction: 1.429
XLogP3-AA: 0.6
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 3
Rotatable Bond Count: 5
Exact Mass: 142.062994177 g/mol
Monoisotopic Mass: 142.062994177 g/mol
Topological Polar Surface Area: 43.4Ų
Heavy Atom Count: 10
Computed by PubChem
Formal Charge: 0
Computed by PubChem
Complexity: 149
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
Specifications of Acetoacetic Acid Allyl Ester:
Assay (GC, area%): ≥ 95.0 % (a/a)
Density (d 20 °C/ 4 °C): 1.036 - 1.041
Identity (IR): passes test
Names of Acetoacetic Acid Allyl Ester:
Regulatory process names:
Acetoacetic acid allyl ester
Acetoacetic acid allyl ester
IUPAC names:
2-propenyl acetoacetate
Ally acetoacetate
allyl 3-oxobutanoate
Acetoacetic acid allyl ester
Acetoacetic acid allyl ester
Acetoacetic acid allyl ester
Allylaceto acetate
prop-2-en-1-yl 3-oxobutanoate
Other identifier:
1118-84-9