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454974

Sigma-Aldrich

mono-2-(Methacryloyloxy)ethyl succinate

Synonym(s):

2-(Methacryloyloxy)ethyl hydrogen succinate, 2-Methacryloyloxyethyl succinate, 3-[2-(Methacryloyloxy)ethoxycarbonyl]propionic acid, 4-[2-(Methacryloyloxy)ethoxy]-4-oxobutanoic acid, Methacryloyloxyethyl succinate, Monomethacryloyloxyethyl succinate

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About This Item

Linear Formula:
H2C=C(CH3)CO2CH2CH2O2CCH2CH2CO2H
CAS Number:
20882-04-6
Molecular Weight:
230.21
EC Number:
244-096-4
MDL number:
MFCD00274302
UNSPSC Code:
12162002
PubChem Substance ID:
24869001
NACRES:
NA.23
Pricing and availability is not currently available.

contains

750 ppm monomethyl ether hydroquinone as inhibitor

refractive index

n20/D 1.464 (lit.)

bp

267 °C (lit.)

density

1.19 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

CC(=C)C(=O)OCCOC(=O)CCC(O)=O

InChI

1S/C10H14O6/c1-7(2)10(14)16-6-5-15-9(13)4-3-8(11)12/h1,3-6H2,2H3,(H,11,12)

InChI key

ZEWLHMQYEZXSBH-UHFFFAOYSA-N

Related Categories

General description

mono-2-(Methacryloyloxy)ethyl succinate(MMES) belongs to methacrylate class of monomers. It is widely used as a monomer to produce polymer coatings with enhanced adhesion, durability, and resistance to chemicals. It can be incorporated into adhesive formulations as it forms strong bonds between various substrates such as metals, plastics, and composites. MMES is compatible with photopolymerization processes and can be used to fabricate UV-curable coatings, inks, and dental restorative materials. It is also used to prepare photocatalysts for wastewater treatment. [1] [2] [3]

Application

mono-2-(Methacryloyloxy)ethyl succinate can be used as:
  • A monomer to prepare peptide-polymer matrix to fabricate multifunctional adhesive hybrid resin composites for dental restorations. MMES has one carboxylic acid functional group for peptide conjugation and a double bond for copolymerization with the polymer matrix.[1]
  • A precursor to synthesize CsPbBr3-based elastomers for flexible optoelectronic devices. The incorporation of MMES helps to improve elasticity, shape recovery, and flexibility.[2]
  • A monomer to synthesize poly(MMES-co-GDMA) monosized microbeads to prepare a multifunctional gold nanocatalyst for the removal of organic pollutant 4-Nitrophenol. MMES contributes to the polymer matrix formation, attachment of gold nanoparticles, and enables the catalyst to exhibit magnetic properties.[3]

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H317,H318

Hazard Classifications

Eye Dam. 1 - Skin Sens. 1A

Storage Class Code

10 - Combustible liquids

WGK

WGK 1

Flash Point(F)

324.5 °F - closed cup

Flash Point(C)

162.5 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
WXBF1138V
MKCT5637
MKCQ6036
MKCP4898
MKCL5059

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Bioinspired multifunctional adhesive system for next generation bio-additively designed dental restorations
Rizacan Sarikaya, et al.
Journal of the Mechanical Behavior of Biomedical Materials, 113, 104135-104135 (2021)
Luminescent and ultrastable perovskite-acrylate based elastomers with excellent stretchability and self-healing capability for flexible backlight display
Aizhao Pan, et al.
Chemical Engineering Journal, 433, 133590-133590 (2022)
Alexandra Muñoz-Bonilla et al.
Polymers, 12(12) (2020-12-03)
Several hydrogels based on 2-hydroxyethyl methacrylate and a methacrylic monomer containing a thiazole group in its lateral chain have been prepared by thermal polymerization at 60 °C in water solution varying the chemical composition of the gels. The posterior quaternization

Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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