2-(Methacryloyloxy)ethyl Acetoacetate

2-(Methacryloyloxy)ethyl Acetoacetate

Product Introduction

2-(Methacryloyloxy)ethyl acetoacetate Basic information
Product Name: 2-(Methacryloyloxy)ethyl acetoacetate
Synonyms: 3-oxo-butanoicaci2-[(2-methyl-1-oxo-2-propenyl)oxy]ethylester;2-(Methacryloyloxy)ethyl acetoacetate,(2-Acetoacetoxy)ethyl methacrylate, AAEM, Ethylene glycol monoacetoacetate monomethacrylate, Lonzamon AAMEA PQ;2-(METHACRYLOYLOXY)E;Monomer AAEMA;ACETOACETIC ACID 2-(METHACRYLOYLOXY)ETHYL ESTER;ACETOACETOXY ETHYL 2-METHYLACRYLATE;ACETOACETOXYETHYL METHACRYLATE;AAEM
CAS: 21282-97-3
MF: C10H14O5
MW: 214.22
EINECS: 244-311-1
Product Categories: monomer
Mol File: 21282-97-3.mol
2-(Methacryloyloxy)ethyl acetoacetate Structure
 
2-(Methacryloyloxy)ethyl acetoacetate Chemical Properties
Melting point <25 °C
Boiling point 100 °C/0.8 mmHg (lit.)
density 1.122 g/mL at 25 °C (lit.)
vapor pressure 0.24Pa at 25℃
refractive index n20/D 1.456
Fp >230 °F
solubility Insoluble in water
form clear liquid
pka 10.16±0.46(Predicted)
color Light yellow to Yellow to Orange
Specific Gravity 1.122
Water Solubility 18.5g/L at 25℃
BRN 2099809
LogP 0.9 at 25℃
CAS DataBase Reference 21282-97-3(CAS DataBase Reference)
EPA Substance Registry System 2-[Methacryloyloxy]ethyl acetoacetate (21282-97-3)
 
Safety Information
Hazard Codes T,Xi
Risk Statements 36/37/38-43
Safety Statements 26-36/37-45-36
RIDADR UN 2810 6.1/PG 3
WGK Germany 3
RTECS AK5600000
HS Code 29189990
 
MSDS Information
Provider Language
SigmaAldrich English
ACROS English
 
2-(Methacryloyloxy)ethyl acetoacetate Usage And Synthesis
Chemical Properties Clear liquid. Acetoacetoxyethyl Methacrylate [21282- 97-3], AAEM, has a pendant acetoacetoxyethyl group which can modify the physical properties of acrylic polymers by decreasing solution viscosity and lowering the glass transition temperature. In addition, the acetoacetyl group contains an active methylene group and a carbonyl group, which can be used to modify or cross-link the polymer [107].
Uses LONZAMON(R) AAEMA is a special methacrylic ester monomer with a reactive methylene group. It is suitable as comonomer for adhesives and coatings as well as copolymer for emulsion polymerisation.
Uses 2-(Methacryloyloxy)ethyl acetoacetate is a methylene active compound that may be used in the synthesis of 2-(methacryloyloxy)ethyl 6-methyl-2-oxo-4-phenyl-1,2,3,4- tetrahydropyrimidine-5-carboxylate. It may be used as a polymerizable chelating agent for metal alkoxides to form polymerizable oxide precursors.
Flammability and Explosibility Non flammable
Mode of action The sol-gel polymerization of Si Ti Zr sols is interesting due to the possibility of controlling several properties such as the refractive index, the thermal expansion coefficient, and the resistance against alkaline corrosion attack in the final products (i.e., optical devices, photonics, sensors, and catalysts). The polymerization route can be directed toward the formation of a hybrid organic-inorganic system using a modifying agent such as 2-(methacryloyloxy) ethyl acetoacetate (MEEAH), that can act as a bidentate (bridging or chelating) agent and offers the possibility of being organically polymerizable due to the presence of unsaturated C C bonds in the molecule. The presence of C-C bonds in MEEAH allowed to perform simultaneously the organic and inorganic polymerization while maintaining the homogeneity of the sols and gels. Regarding the partial charge values, in all cases, δ(MEEA?) are negative, indicating that it can easily bond Ti and Zr. On the other hand, δ(OPrn) and δ(OPri ) values are positive in all the molecules where MEEA? is also present, and therefore those species (OPrn and OPri ) are labile[1].
References [1] J. Méndez-Vivar. "The Role of 2-(Methacryloyloxy) Ethyl Acetoacetate in the Polymerization of Hybrid Multicomponent (Si, Ti, Zr) Sols." Journal of Sol-Gel Science and Technology 25 3 (2002): 249–254.
 
2-(Methacryloyloxy)ethyl acetoacetate Preparation Products And Raw materials
Raw materials Ethyl acetoacetate-->2-Hydroxyethyl methacrylate-->2,2,6-Trimethyl-4H-1,3-dioxin-4-one

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