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128635

Sigma-Aldrich

2-Hydroxyethyl methacrylate

contains ≤250 ppm monomethyl ether hydroquinone as inhibitor, 97%

Synonym(s):

1,2-Ethanediol mono(2-methylpropenoate), Glycol methacrylate, HEMA

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About This Item

Linear Formula:
CH2=C(CH3)COOCH2CH2OH
CAS Number:
868-77-9
Molecular Weight:
130.14
Beilstein/REAXYS Number:
1071583
EC Number:
212-782-2
MDL number:
MFCD00002863
UNSPSC Code:
12162002
PubChem Substance ID:
24847870
NACRES:
NA.23

vapor density

5 (vs air)

Quality Level

200

vapor pressure

0.01 mmHg ( 25 °C)

assay

97%

form

liquid

contains

≤250 ppm monomethyl ether hydroquinone as inhibitor

refractive index

n20/D 1.453 (lit.)

bp

67 °C/3.5 mmHg (lit.)

density

1.073 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

CC(=C)C(=O)OCCO

InChI

1S/C6H10O3/c1-5(2)6(8)9-4-3-7/h7H,1,3-4H2,2H3

InChI key

WOBHKFSMXKNTIM-UHFFFAOYSA-N

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General description

2-Hydroxyethyl methacrylate (HEMA) was the first monomer to be used to synthesize hydrogels for biomedical applications.The water swelling properties of HEMA are enhanced by copolymerization with more hydrophilic monomers.HEMA finds wide applications for drug delivery.

Application

HEMA is used in the synthesis of biologically functional poly (2-hydroxyethyl methacrylate) (PHEMA) coplymers. It is also used to prepare light responsive membranes of PHEMA, HEMA/ acrylamide based specific drug release hydrogel, and water soluble HEMA/methacrylic acid hydrogel for drug delivery. Effects of HEMA on the migration of dental pulp stem cells (in vitro) may be studied.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - Skin Sens. 1

Storage Class

10 - Combustible liquids

wgk_germany

WGK 1

flash_point_f

222.8 °F - closed cup

flash_point_c

106 °C - closed cup

Certificates of Analysis (COA)

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Preparation of Light-responsive Membranes by a Combined Surface Grafting and Postmodification Process.
Scholler K, et al.
Journal of Visualized Experiments, 85, e51680-e51680 (2014)
Drake W Williams et al.
Journal of endodontics, 39(9), 1156-1160 (2013-08-21)
Cell migration is an important step in pulpal wound healing. Although components in the resin-based dental materials are known to have adverse effects on pulp wound healing including proliferation and mineralization, their effects on cell migration have been scarcely examined.
Influence of the ionic character of a drug on its release rate from hydrogels based on 2-hydroxyethylmethacrylate and acrylamide synthesized by photopolymerization
Gomez ML, et al.
Express Polymer Letters, 6(30, 189-197 (2012)
Thomas J Dursch et al.
Biomaterials, 35(2), 620-629 (2013-10-24)
Two-photon confocal microscopy and back extraction with UV/Vis-absorption spectrophotometry quantify equilibrium partition coefficients, k, for six prototypical drugs in five soft-contact-lens-material hydrogels over a range of water contents from 40 to 92%. Partition coefficients were obtained for acetazolamide, caffeine, hydrocortisone
Loretta A Idowu et al.
Polymers, 11(3) (2019-04-10)
2-Hydroxyethyl methacrylate (HEMA) is an important component of many acrylic resins used in coatings formulations, as the functionality ensures that the chains participate in the cross-linking reactions required to form the final product. Hence, the knowledge of their radical copolymerization
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Articles

Continuous Flow Manufacturing for Monomer Synthesis

The manufacture of monomers for use in ophthalmic applications is driven by the need for higher purity, improved reliability of manufacturing supply, but ultimately by the need for the increased comfort, convenience, and safety of contact lens wearers. Daily wear contact lenses have the potential to fill this need for many customers; however, their widespread use is constrained by higher costs compared to weekly- or monthly-based lenses. New approaches that improve cost structure and result in higher quality raw materials are needed to help make contact lenses more affordable and accelerate growth of the contact lens market.

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