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

Flash point:

>230 °F

solubility 

Insoluble in water

form 

clear liquid

pka

10.16±0.46(Predicted)

Specific Gravity

1.122

color 

Light yellow to Yellow to Orange

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

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

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 (21282-97-3)Related Product Information

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