(Hydroxyethyl)methacrylate

(Hydroxyethyl)methacrylate
Names


IUPAC name 2-Hydroxyethyl 2-methylprop-2-enoate
Other names HEMA; Hydroxyethylmethacrylate; Glycol methacrylate; Glycol monomethacrylate; Hydroxyethyl methacrylate; Ethylene glycol methacrylate; 2-(Methacryloyloxy)ethanol
Identifiers
CAS Registry Number	868-77-9^Y
ChEBI	CHEBI:34288^Y
ChemSpider	12791^Y
InChI InChI=1S/C6H10O3/c1-5(2)6(8)9-4-3-7/h7H,1,3-4H2,2H3^Y Key: WOBHKFSMXKNTIM-UHFFFAOYSA-N^Y InChI=1/C6H10O3/c1-5(2)6(8)9-4-3-7/h7H,1,3-4H2,2H3 Key: WOBHKFSMXKNTIM-UHFFFAOYAH
Jmol-3D images	Image Image
KEGG	C14530^Y
SMILES O=C(OCCO)\C(=C)C CC(=C)C(=O)OCCO
UNII	6E1I4IV47V^Y
Properties
Molecular formula	C₆H₁₀O₃
Molar mass	130.14 g·mol⁻¹
Appearance	colourless liquid
Density	1.07
Melting point	−99 °C (−146 °F; 174 K)^[1]
Boiling point	213 °C (415 °F; 486 K)^[1]
Vapor pressure	0.08 hPa
Hazards
Main hazards	eye irritation
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Y verify (what is: Y/N?)
Infobox references

Hydroxyethylmethacrylate or HEMA is the monomer that is used to make the polymer polyhydroxyethylmethacrylate. The polymer is hydrophobic; however, when the polymer is subjected to water it will swell due to the molecule's hydrophilic pendant group. Depending on the physical and chemical structure of the polymer, it is capable of absorbing from 10 to 600% water relative to the dry weight. Because of this property, it was one of the first materials to be successfully used in the manufacture of flexible contact lenses^[2]

References

↑ 1.0 1.1 "GPS Safety Summary 2-Hydroxyethyl methacrylate (HEMA)". July 2013.
↑ Blasco, Joe; Kehoe, Vincent J-R; The professional make-up artist : motion pictures, television, print, theatre; ISBN 0-9771580-0-4; LCC# PN2068.B53 2005