Ethylene glycol dimethacrylate

Ethylene glycol dimethylacrylate (EGDMA) is a diester formed by condensation of two equivalents of methacrylic acid and one equivalent of ethylene glycol.^[2]

Ethylene glycol dimethacrylate^[1]

Names
Preferred IUPAC name Ethane-1,2-diyl bis(2-methylprop-2-enoate)
Other names Methacrylic acid, ethylene ester; 1,2-Bis(methacryloyloxy)ethane; 1,2-Ethanediol dimethacrylate; Diglycol dimethacrylate; Ethanediol dimethacrylate; Ethylene dimethacrylate; Ethylene glycol bis(methacrylate); Ethylene glycol dimethacrylate; Ethylene methacrylate; 2-(Methacryloyloxy)ethyl methacrylate
Identifiers
CAS Number	97-90-5 Y
3D model (JSmol)	Interactive image
Abbreviations	EGDMA
Beilstein Reference	1776663
ChEBI	CHEBI:53436 Y
ChEMBL	ChEMBL1709582
ChemSpider	7077 Y
ECHA InfoCard	100.002.380
EC Number	202-617-2
Gmelin Reference	637376
PubChem CID	7355
RTECS number	OZ4400000
UNII	7BK5G69305 Y
CompTox Dashboard (EPA)	DTXSID20891154 DTXSID1026615, DTXSID20891154
InChI InChI=1S/C10H14O4/c1-7(2)9(11)13-5-6-14-10(12)8(3)4/h1,3,5-6H2,2,4H3 Y Key: STVZJERGLQHEKB-UHFFFAOYSA-N Y
SMILES CC(=C)C(=O)OCCOC(=O)C(=C)C
Properties
Chemical formula	C10H14O4
Molar mass	198.218 g·mol−1
Density	1.051 g/mL
Melting point	−40 °C (−40 °F; 233 K)
Boiling point	98 to 100 °C (208 to 212 °F; 371 to 373 K) (5 mmHg)
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H317, H319, H335, H412
Precautionary statements	P261, P264, P271, P272, P273, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P333+P313, P337+P313, P362, P363, P403+P233, P405, P501
Flash point	101 °C (214 °F; 374 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

EGDMA can be used in free radical copolymer crosslinking reactions. When used with methyl methacrylate, it leads to gel point at relatively low concentrations because of the nearly equivalent reactivities of all the double bonds involved.

It is used as a monomer to prepare hydroxyapatite/poly methyl methacrylate composites. EGDMA can be used in free radical copolymer crosslinking reactions.

Its toxicity profile has been fairly well studied.^[3] It is sometimes called ethylene dimethacrylate.^[4]

References

1. "Ethylene glycol dimethacrylate". Sigma-Aldrich.
2. Bielstein 2, IV, 1532
3. Bielecka-Kowalska, Anna; Czarny, Piotr; Wigner, Paulina; Synowiec, Ewelina; Kowalski, Bartosz; Szwed, Marzena; Krupa, Renata; Toma, Monika; Drzewiecka, Malgorzata; Majsterek, Ireneusz; Szemraj, Janusz; Sliwinski, Tomasz; Kowalski, Michał (March 2018). "Ethylene glycol dimethacrylate and diethylene glycol dimethacrylate exhibits cytotoxic and genotoxic effect on human gingival fibroblasts via induction of reactive oxygen species". Toxicology in Vitro. 47: 8–17. doi:10.1016/j.tiv.2017.10.028.
4. PubChem. "Ethylene glycol dimethacrylate". pubchem.ncbi.nlm.nih.gov. Retrieved 2023-03-16.