mono-2-(Methacryloyloxy)ethyl succinate: Properties & Applications

mono-2-(Methacryloyloxy)ethyl succinate is a bifunctional methacrylate monomer bearing a free carboxylic acid group, enabling its use as a reactive building block in polymer synthesis, hydrogel fabrication, and surface-functionalization applications.

Product SKU

M486865

Molecular Formula

C10H14O7

Molecular Weight

Approximately 246.21 g/mol

Key Functional Groups

Methacrylate ester and free carboxylic acid

Primary Application

Reactive monomer for polymerization and hydrogel synthesis

Reference Standard

Comparable to Sigma-Aldrich catalog No. 454974

Chemical Identity and Structure

mono-2-(Methacryloyloxy)ethyl succinate (CAS number to be confirmed; see review flags) is the monoester product formed by the reaction of 2-hydroxyethyl methacrylate (HEMA) with succinic anhydride. The resulting molecule retains the polymerizable methacrylate double bond at one terminus and presents a free carboxylic acid group derived from the succinyl spacer at the other. This dual functionality — a vinyl group for radical polymerization and a carboxylate for further conjugation or ionic interaction — makes it structurally distinct from simple methacrylate monomers.

The succinyl linker introduces a four-carbon flexible spacer between the methacrylate backbone and the carboxylic acid, which can influence the hydrophilicity, glass-transition temperature, and inter-chain interactions of resulting polymers. The free carboxylic acid (pKa typically in the range of 4–5 for succinic acid derivatives) can participate in hydrogen bonding, ionic crosslinking, or chemical coupling reactions under mild conditions.

Synthesis and Physicochemical Properties

The compound is typically synthesized by ring-opening esterification of succinic anhydride with 2-hydroxyethyl methacrylate in the presence of a base catalyst or nucleophilic promoter, often at mild temperatures to prevent premature polymerization of the methacrylate group. An inhibitor such as hydroquinone or monomethyl ether hydroquinone (MEHQ) is commonly included during synthesis and storage to suppress radical-initiated homopolymerization.

Key physicochemical parameters include: a molecular weight of approximately 246.21 g/mol, the presence of two ester linkages rendering the compound susceptible to hydrolysis under strongly acidic or basic conditions, and moderate water solubility attributable to the carboxylic acid and ester groups. The compound is typically handled and stored as a liquid or low-melting solid at low temperatures (2–8 °C) and protected from light and oxidizing agents to preserve the vinyl functionality.

Note: Specific melting point, boiling point, density, and purity specifications for SKU M486865 should be confirmed against the current Aladdin Scientific Certificate of Analysis prior to experimental use.

Research Applications

Polymer and Hydrogel Synthesis: The methacrylate group allows incorporation of mono-2-(Methacryloyloxy)ethyl succinate into addition polymers via free-radical, RAFT, ATRP, or other controlled polymerization techniques. Introduction of pendant carboxylic acid groups along a polymer backbone imparts pH-responsive behavior, making the resulting materials relevant for stimuli-responsive hydrogels, drug delivery matrices, and tissue engineering scaffolds.

Surface Functionalization: The carboxylic acid terminus can be activated (e.g., with EDC/NHS chemistry) to covalently conjugate proteins, peptides, or amine-bearing biomolecules onto polymer-coated surfaces, supporting biosensor development and bioconjugation workflows.

Dental and Adhesive Materials Research: Carboxylic acid-functionalized methacrylate monomers are studied as adhesion-promoting components in dental composite resins and adhesives, where the carboxylate moiety interacts with hydroxyapatite mineral surfaces to improve bonding performance. This class of monomers is therefore relevant to research on dental adhesion and restorative materials.

Crosslinked Network Formation: In combination with difunctional crosslinkers, this monomer can contribute to ionically or covalently crosslinked polymer networks useful in controlled-release formulations and stimuli-responsive coatings.

Handling, Storage, and Safety Considerations

As with most methacrylate monomers, mono-2-(Methacryloyloxy)ethyl succinate should be handled with appropriate personal protective equipment including chemical-resistant gloves, safety glasses, and lab coat. Work should be conducted in a well-ventilated area or fume hood to minimize inhalation exposure to vapor or aerosol.

The compound should be stored at 2–8 °C in a tightly sealed container away from heat, light, and oxidizing agents. An inhibitor is typically present in the commercial product; removal of the inhibitor prior to polymerization (if required by the application) should be performed with caution, as uninhibited material may polymerize exothermically if exposed to heat, light, or radical initiators.

Researchers should consult the current Safety Data Sheet (SDS) for SKU M486865 available from Aladdin Scientific for detailed hazard classification, first-aid measures, disposal guidance, and regulatory information before use.

Note: Specific GHS hazard classifications and R/S or H/P statements for M486865 should be verified against the current Aladdin SDS.

Frequently asked questions

What is the primary difference between mono-2-(Methacryloyloxy)ethyl succinate and 2-hydroxyethyl methacrylate (HEMA)?

HEMA contains a hydroxyl group at the non-methacrylate terminus, whereas mono-2-(Methacryloyloxy)ethyl succinate is derived from HEMA by ring-opening reaction with succinic anhydride, replacing the hydroxyl with a succinyl ester linkage that terminates in a free carboxylic acid. This carboxylic acid group substantially expands the reactivity of the monomer, enabling pH-responsive polymer behavior and post-polymerization bioconjugation that HEMA alone cannot provide.

Can this monomer be copolymerized with other methacrylate or acrylate monomers?

Yes. mono-2-(Methacryloyloxy)ethyl succinate is a vinyl monomer compatible with free-radical copolymerization alongside common monomers such as methyl methacrylate, acrylamide, or other hydroxyalkyl methacrylates. Controlled radical polymerization techniques such as RAFT and ATRP can also be applied to achieve defined molecular weights and narrow dispersity in copolymer systems. The carboxylic acid group may require protection or pH adjustment in certain polymerization media.

How should the inhibitor be handled if I need to remove it before polymerization?

Inhibitors such as MEHQ are commonly removed by passing the monomer through an activated alumina or inhibitor-removal resin column immediately before use. The purified monomer must then be handled with great care under inert atmosphere and used promptly, as uninhibited monomers are susceptible to spontaneous radical polymerization upon exposure to air, light, or elevated temperature. Confirm the inhibitor type and recommended removal procedure from the Aladdin Scientific product SDS or Certificate of Analysis for SKU M486865.

Is mono-2-(Methacryloyloxy)ethyl succinate suitable for biomedical applications?

The carboxylic acid functionality and methacrylate polymerizability make this monomer a candidate building block for pH-responsive hydrogels, drug delivery vehicles, and bioconjugation platforms studied in biomedical research. However, suitability for any specific biomedical application depends on the purity grade, polymerization conditions, cytotoxicity data, and regulatory requirements relevant to the intended use. Researchers should conduct appropriate biocompatibility assessments and consult current literature before use in biological systems.

References

1. Sigma-Aldrich product page for mono-2-(Methacryloyloxy)ethyl succinate, catalog No. 454974. Merck KGaA, Darmstadt, Germany.
2. Odian, G. Principles of Polymerization, 4th ed.; Wiley-Interscience: Hoboken, NJ, 2004. General reference for radical and controlled polymerization of methacrylate monomers.
3. Van Landuyt, K.L. et al. Systematic review of the chemical composition of contemporary dental adhesives. Biomaterials 2007, 28, 3757–3785. doi:10.1016/j.biomaterials.2007.04.044

Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.