ALLYL ACETOACETATE

ALLYL ACETOACETATE

Allyl acetoacetate 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, Allyl acetoacetate 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 Allyl acetoacetate 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

Allyl acetoacetate is an organic compound that is the simplest member of the acetic acid esters.

Allyl acetoacetate can be synthesized by reacting allyl alcohol with hydrochloric acid and a particle.

Allyl acetoacetate is a clear colorless liquid.

Allyl acetoacetate has been shown to have cytotoxic effects on cardiac tissues, as well as certain reactive properties, which may be due to Allyl acetoacetate’s ability to form cross-links with proteins.

Allyl acetoacetate is registered under the REACH Regulation but is not currently being manufactured in and / or imported to the European Economic Area.

Allyl acetoacetate is an adhesion promoter.

Allyl acetoacetate is available in colorless to pale yellow colored liquid form.

Allyl acetoacetate is recommended for coatings.

Allyl acetoacetate holds significant importance as an organic compound widely utilized in chemical synthesis and scientific exploration.

As a colorless liquid with a potent fragrance, Allyl acetoacetate effortlessly dissolves in various organic solvents.

Allyl acetoacetate’s versatility in the synthesis of numerous compounds makes Allyl acetoacetate a valuable asset.

Moreover, Allyl acetoacetate plays a role in the creation of polymers, dyes, and catalysts.

Fascinatingly, Allyl acetoacetate finds application in the synthesis of essential biochemicals, such as vitamins, hormones, and enzymes.

In scientific research, particularly in organic synthesis, Allyl acetoacetate is highly regarded and employed.

The reaction involving allyl alcohol and acetic anhydride in the presence of a catalyst results in Allyl acetoacetate 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 Allyl acetoacetate an indispensable component in various scientific and industrial endeavors.

Allyl acetoacetate is registered under the REACH Regulation but is not currently being manufactured in and / or imported to the European Economic Area.

Allyl acetoacetate is used in formulation or re-packing.

Allyl acetoacetate is an adhesion promoter.

Allyl acetoacetate is available in colorless to pale yellow colored liquid form.

Allyl acetoacetate is recommended for coatings.

Allyl acetoacetate is an organic compound that is the simplest member of the acetic acid esters.

Allyl acetoacetate can be synthesized by reacting allyl alcohol with hydrochloric acid and a particle.

Allyl acetoacetate has been shown to have cytotoxic effects on cardiac tissues, as well as certain reactive properties, which may be due to Allyl acetoacetate’s ability to form cross-links with proteins.

Allyl acetoacetate is also used as a cross-linking agent for polyvinyl chloride plastics.

Allyl acetoacetate is an organic ester with the chemical formula C7H10O3.

Allyl acetoacetate is a colorless to light yellow liquid characterized by its pleasant odor.

Allyl acetoacetate is used primarily as a chemical intermediate in organic synthesis, where Allyl acetoacetate serves as a building block for the production of a variety of complex molecules, including pharmaceuticals, agrochemicals, and specialty polymers.

Allyl acetoacetate is a versatile organic compound with a range of applications in chemical synthesis, polymer production, and occasionally in the flavor and fragrance industry.

Allyl acetoacetate’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 Allyl Acetoacetate:

Allyl acetoacetate is also used as a cross-linking agent for polyvinyl chloride plastics.

Allyl acetoacetate is used in the formulation of pharmaceuticals and as an intermediate for fine chemicals.

Allyl acetoacetate is used in formulation or re-packing.

Release to the environment of Allyl acetoacetate can occur from industrial use: formulation of mixtures.

Moreover, Allyl acetoacetate plays a role in the creation of polymers, dyes, and catalysts.

Fascinatingly, Allyl acetoacetate finds application in the synthesis of essential biochemicals, such as vitamins, hormones, and enzymes.

In scientific research, particularly in organic synthesis, Allyl acetoacetate is highly regarded and employed.

The reaction involving allyl alcohol and acetic anhydride in the presence of a catalyst results in Allyl acetoacetate 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 Allyl acetoacetate an indispensable component in various scientific and industrial endeavors.

Applications of Allyl Acetoacetate:

Chemical Synthesis:

Allyl acetoacetate is commonly used as an intermediate in the synthesis of more complex organic compounds.

Allyl acetoacetate’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:

Allyl acetoacetate 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, Allyl acetoacetate is sometimes used in the formulation of flavors and fragrances, although this is less common than its use in industrial chemical synthesis.

Production of Allyl Acetoacetate:

The production of Allyl acetoacetate 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 Allyl acetoacetate 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 Allyl acetoacetate 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 Allyl acetoacetate from unreacted starting materials and by-products.

Alternatively, Allyl acetoacetate can be washed with water and dried over anhydrous sodium sulfate or other drying agents to remove any remaining water.

Final Product:

The purified Allyl acetoacetate is collected as a colorless to light yellow liquid, ready for use in various chemical synthesis applications.

Handling And Storage of Allyl Acetoacetate:

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 Allyl Acetoacetate:

Chemical stability:

Allyl acetoacetate is chemically stable under standard ambient conditions (room temperature).

Incompatible materials:

No data available

First Aid Measures of Allyl Acetoacetate:

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 Allyl Acetoacetate:

Suitable extinguishing media:

Water

Foam

Carbon dioxide (CO2)

Dry powder

Unsuitable extinguishing media:

For Allyl acetoacetate 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 Allyl Acetoacetate:

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 Allyl Acetoacetate:

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 Allyl Acetoacetate:

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 Allyl Acetoacetate:

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: Allyl acetoacetate

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 Allyl Acetoacetate:

Assay (GC, area%): ≥ 95.0 % (a/a)

Density (d 20 °C/ 4 °C): 1.036 – 1.041

Identity (IR): passes test

Names of Allyl Acetoacetate:

Regulatory process names:

Allyl acetoacetate

Allyl acetoacetate

IUPAC names:

2-propenyl acetoacetate

Ally acetoacetate

allyl 3-oxobutanoate

Allyl acetoacetate

Allyl acetoacetate

Allyl acetoacetate

Allylaceto acetate

prop-2-en-1-yl 3-oxobutanoate

Other identifier:

1118-84-9