ALLYL ACETOACETATE

Allyl Acetoacetate is used as a cross-linking agent for polyvinyl chloride plastics and thermosetting polymers, improving their mechanical properties and thermal stability.
Due to its pleasant odor, Allyl Acetoacetate is sometimes used in formulating flavors and fragrances, although this is less common than its use in industrial chemical synthesis.

CAS Number: 1118-84-9
EC Number: 214-269-9
MDL number: MFCD00009811
Linear Formula: CH3COCH2COOCH2CH=CH2
Molecular Formula: C7H10O3
Molecular Weight (g/mol): 142.154 

SYNONYMS:
Allyl acetoacetate, Acetoacetic acid allyl ester, 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, 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, acetoacetic acid, allyl ester, allyl 3-oxobutanoate, allyl acetylacetate, butanoic acid, 3-oxo-, 2-propen-1-yl ester, butanoic acid, 3-oxo-, 2-propenyl ester, 3-oxo- butyric acid allyl ester, prop-2-enyl 3-oxobutanoate, (2- propenyl) 3-oxobutanoate

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.
Its 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.

USES and APPLICATIONS of ALLYL ACETOACETATE:
Organic Synthesis uses of Allyl Acetoacetate: Intermediate in the synthesis of pharmaceuticals, agrochemicals, and other fine chemicals
Polymer Industry: Allyl Acetoacetate is used as a monomer or comonomer in the production of specialty polymers and resins, imparting properties like flexibility and chemical resistance

Flavor and Fragrance: Allyl Acetoacetate is employed in the formulation of flavors and fragrances due to its fruity aroma
Adhesion Promoter: Allyl Acetoacetate is utilized in coatings to enhance adhesion properties

-Cross-Linking Agent: 
Allyl Acetoacetate is applied in the production of cross-linked polymers, such as polyvinyl chloride (PVC)
Allyl Acetoacetate is used in the formulation of pharmaceuticals and as an intermediate for fine chemicals

-Organic Synthesis uses of Allyl Acetoacetate:
*Pharmaceutical Intermediates: 
Allyl Acetoacetate is used in synthesizing various pharmaceutical compounds, including antibiotics and anti-inflammatory agents.

*Prodrug Formulation: 
Research is ongoing into its potential use as a prodrug, where Allyl Acetoacetate could be converted into active drugs within the body, improving drug delivery systems.

-Polymer and Material Science uses of Allyl Acetoacetate_
*Monomer/Comonomer: 
Allyl Acetoacetate acts as a monomer or comonomer in creating specialized polymers and copolymers, contributing properties such as flexibility, durability, and chemical resistance.

*Cross-Linking Agent:
Allyl Acetoacetate is used as a cross-linking agent for polyvinyl chloride plastics and thermosetting polymers, improving their mechanical properties and thermal stability.

-Flavor and Fragrance Industry uses of Allyl Acetoacetate:
*Aroma Compound: 
Due to its pleasant odor, Allyl Acetoacetate is sometimes used in formulating flavors and fragrances, although this is less common than its use in industrial chemical synthesis.

-Agricultural Applications of Allyl Acetoacetate:
*Herbicides and Insecticides: 
Allyl Acetoacetate serves as an intermediate in synthesizing herbicides and insecticides, contributing to effective pest management strategies.

*Plant Growth Regulators: 
Research into Allyl Acetoacetate's use as a plant growth regulator suggests potential benefits for enhancing crop yields and improving 

-Environmental Chemistry uses of Allyl Acetoacetate:
*Pollutant Removal: 
Studies are being conducted on Allyl Acetoacetate's efficacy for removing pollutants from water and soil, highlighting its role in sustainable environmental practices.

*Green Chemistry Initiatives: 
Allyl Acetoacetate is investigated within green chemistry frameworks aimed at developing more environmentally friendly chemical processes

CHEMICAL BEHAVIOR OF ALLYL ACETOACETATE:
Allyl Acetoacetate contains both ester and ketone functional groups, making it versatile in chemical reactions:

*Michael Addition Reactions: 
Allyl Acetoacetate acts as a nucleophile, forming carbon-carbon bonds crucial in constructing complex organic frameworks.

*Fischer Indole Synthesis: 
Allyl Acetoacetate is employed to produce indole derivatives, significant in medicinal chemistry due to their biological activity.

*Condensation Reactions: 
Allyl Acetoacetate involved in forming β-dicarbonyl compounds, expanding its utility in synthetic pathways.

*Cross-Linking: 
Allyl Acetoacetate can undergo self-crosslinking reactions, particularly when combined with amines or other functional groups, enhancing material properties in coatings and polymers.

FUNCTIONAL GROUPS OF ALLYL ACETOACETATE:
Ester and ketone

REACTIVITY OF ALLYL ACETOACETATE:
*Allyl Acetoacetate participates in Michael addition reactions
*Allyl Acetoacetate undergoes transesterification with alcohols
*Allyl Acetoacetate can polymerizes under certain conditions
*Allyl Acetoacetate acts as a nucleophile in various organic synthesis reactions

PHYSICAL and CHEMICAL 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
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
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

Water Solubility: 50 g/L (20 ºC)
Molecular Weight: 142.15 g/mol
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
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
Boiling point: 87 - 91 °C (13 hPa)

Density: 1.037 g/cm3
Explosion limit: 1.15 %(V)
Flash point: 67 °C
Ignition temperature: 300 °C
Melting Point: <-70 °C
pH value: 3.7 (48 g/l, H₂O, 20 °C)
Vapor pressure: 1 hPa (20 °C)
Solubility: 48 g/l
Appearance: colorless to pale yellow clear liquid (est)
Assay: 95.00 to 100.00

Food Chemicals Codex Listed: No
Melting Point: -85.00 °C. @ 760.00 mm Hg
Boiling Point: 196.00 °C. @ 760.00 mm Hg
Vapor Pressure: 0.501000 mmHg @ 25.00 °C. (est)
Flash Point: 168.00 °F. TCC (75.56 °C.)
logP (o/w): 0.703 (est)
Soluble in:
alcohol
water, 6.089e+004 mg/L @ 25 °C (est)
Insoluble in: water

Physical state: liquid
Color: colorless
Odor: No data available
Melting point/freezing point: No data available
Initial boiling point and boiling range: 194 - 195 °C at 983 hPa
Flammability (solid, gas): No data available
Upper/lower flammability or explosive limits: Lower explosion limit: 1,15 %(V)
Flash point: 67 °C - closed cup
Autoignition temperature: No data available
Decomposition temperature: No data available

pH: No data available
Viscosity: 
Viscosity, kinematic: No data available, 
Viscosity, dynamic: No data available
Water solubility: No data available
Partition coefficient: n-octanol/water: log Pow: 0,339 at 25 °C
Vapor pressure: 1 hPa at 20 °C
Density: 1,037 g/cm3

Relative density: No data available
Relative vapor density: No data available
Particle characteristics: No data available
Explosive properties: No data available
Oxidizing properties: No data available
Other safety information: No data available
Molecular Formula / Molecular Weight: C7H10O3 = 142.15
Physical State (20 deg.C): Liquid

Storage Temperature: Room Temperature 
(Recommended in a cool and dark place, <15°C)
CAS RN: 1118-84-9
Reaxys Registry Number: 1758569
PubChem Substance ID: 87559068
MDL Number: MFCD00009811
CAS: 1118-84-9
Molecular Formula: C7H10O3

Molecular Weight (g/mol): 142.154
MDL Number: MFCD00009811
InChI Key: AXLMPTNTPOWPLT-UHFFFAOYSA-N
Melting Point: -85°C
Boiling Point: 195°C
MDL Number: MFCD00009811
UN Number: 2810
InChI Key: AXLMPTNTPOWPLT-UHFFFAOYSA-N
IUPAC Name: prop-2-enyl 3-oxobutanoate

PubChem CID: 70701
Percent Purity: ≥95.0% (GC)
Chemical Name or Material: Allyl Acetoacetate
SMILES: CC(=O)CC(=O)OCC=C
Molecular Weight (g/mol): 142.154
Formula Weight: 142.15
Physical Form: Liquid
Formula: C₇H₁₀O₃
MW: 142.1525 g/mol
Storage Temperature: Ambient
MDL Number: MFCD00009811

CAS Number: 1118-84-9
EINECS: 214-269-9
UN: 2810
ADR: 6.1,III
CAS Number: 1118-84-9
MDL Number: MFCD00009811
Molecular Formula: C7H10O3
Molecular Weight: 142.15
Purity/Analysis Method: 95.0% (GC)
Form: Clear Liquid
Boiling point (°C): 195

Melting point (°C): -85
Flash Point (°C): 76
Specific Gravity (20/20): 1.04
Formula: C₇H₁₀O₃
MW: 142.1525 g/mol
Boiling Pt: 195 °C
Melting Pt: –85 °C
Density: 1.04 (20 °C)
Flash Pt: 76 °C
MDL Number: MFCD00009811

CAS Number: 1118-84-9
UN: 2810
ADR: 6.1,III
Linear Formula: CH3COCH2COOCH2CH=CH2
CAS Number: 1118-84-9
Molecular Weight: 142.15
MDL Number: MFCD00009811
UNSPSC Code: 12352108
EC Index Number: 214-269-9
NACRES: NA.22
Appearance: colorless to pale yellow clear liquid (est)

Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: -85.00 °C @ 760.00 mm Hg
Boiling Point: 196.00 °C @ 760.00 mm Hg
Vapor Pressure: 0.501000 mmHg @ 25.00 °C (est)
Flash Point: 168.00 °F TCC (75.56 °C)
logP (o/w): 0.703 (est)
Soluble in: alcohol, water, 6.089e+004 mg/L @ 25 °C (est)
Insoluble in: water

FIRST AID MEASURES of ALLYL ACETOACETATE:
-Description of first-aid measures:
*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

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.

FIRE FIGHTING MEASURES of ALLYL ACETOACETATE:
-Extinguishing media:
*Suitable extinguishing media:
Water 
Foam 
Carbon dioxide (CO2) 
Dry powder
*Unsuitable extinguishing media:
For this substance/mixture 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.

EXPOSURE CONTROLS/PERSONAL PROTECTION of ALLYL ACETOACETATE:
-Control parameters:
--Ingredients with workplace control parameters:
-Exposure controls.
--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.

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:
The product is chemically stable under standard ambient conditions (room temperature) .
-Incompatible materials:
No data available