02 Feb Ethyl-acetoxyacrylate
Product of the month | February 2023
SP-40-005 is the Ethyl-acetoxyacrylate (EAA), a reactive precursor with a low boiling point (84-85°C) and used in a large range of chemical reactions.
This 2-oxyacrylate functionalized by an acetyl group can be used as monomer in conventional radical polymerization but also in controlled polymerization (eg: MADIX1) with different acrylic monomers leading to copolymers with biodegradability properties2 or/and heat resistance and transparency.3
In addition, this unsaturated precursor is also involved in different organic reactions such as coupling reactions (eg: Heck4), cycloadditions or reductive radical additions.5 This product is a key reactant to access to several innovative synthetic precursors such as monoaryl pyruvates4, lactate derivatives5 or modified nucleosides6.
SP-40-005 is available at 5, 10 or 25g scale and bulk quantities can be synthesized on demand.
References
[1] D. Batt-Coutrot and al., MADIX polymerization of captodative ethyl α-acetoxyacrylate with acrylate monomers: Macromolecular Chemistry and Physics, 206, 17, 1709-1717, (2005) >
[2a] H. Tanaka and al., Dependence of polymer tacticity and polymerization rate on conversion, solvent, chain length in radical polymerization of captodative-substituted ethyl acetoxyacrylate, Polymer Bulletin (Heidelberg, Germany), 79(8), 6547-6564 (2022) >
[2b] C. Loubat and al., Synthesis and monomer reactivity ratios of ethyl α-acetoxyacrylate and acrylic acid copolymers, Polymer International, 54(11), 1557-156 (2005) >
[3] W. Ninomiya and al., An efficient synthesis of α-acyloxyacrylate esters as candidate monomers for bio-based polymers by heteropolyacid-catalyzed acylation of pyruvate esters, Green Chemistry, 11(10), 1666-1674 (2009) >
[4] K. Matcha and al., Heck Reaction of 2-Oxyacrylates with Aryl Bromides: A Common Route to Monoaryl Pyruvates and Ortho Ester-Protected Monoaryl Pyruvates, Journal of Organic Chemistry, 87(16), 10736-10746 (2022) >
[5] J.B. Diccianni and al., Synthesis of lactate derivatives via reductive radical addition to α-oxyacrylates, Tetrahedron, 75(31), 4180-4185 (2019) >
[6] M.G. Saita and al., Diastereo- and Enantioselective Synthesis of 1′-C-Branched N,O-Nucleosides, Nucleosides, Nucleotides & Nucleic Acids, 22(5-8), 739-742 (2003) >
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