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| | 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;ETHYL 2-((2-METHYL-1-OXO-2-PROPENYL)OXY)-3-OXO-BUTANOATE;ETHYLENE GLYCOL MONOACETOACETATE MONOMETHACRYLATE | | 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 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 | | storage temp. | Storage temp. 2-8°C | | solubility | Insoluble in water | | pka | 10.16±0.46(Predicted) | | form | clear liquid | | color | Light yellow to Yellow to Orange | | Specific Gravity | 1.122 | | Water Solubility | 18.5g/L at 25℃ | | BRN | 2099809 | | Cosmetics Ingredients Functions | FILM FORMING | | Cosmetic Ingredient Review (CIR) | 2-(Methacryloyloxy)ethyl acetoacetate (21282-97-3) | | InChI | 1S/C10H14O5/c1-7(2)10(13)15-5-4-14-9(12)6-8(3)11/h1,4-6H2,2-3H3 | | InChIKey | IBDVWXAVKPRHCU-UHFFFAOYSA-N | | SMILES | CC(=O)CC(=O)OCCOC(=O)C(C)=C | | 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) |
| 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 | | TSCA | TSCA listed | | HS Code | 29189990 | | Storage Class | 10 - Combustible liquids |
| | 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.
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| | 2-(Methacryloyloxy)ethyl acetoacetate Preparation Products And Raw materials |
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