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8.00609

Sigma-Aldrich

2,3-Epoxypropyl methacrylate

Technipur®, for synthesis

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Synonym(s):
Glycidyl methacrylate, 2-((Methacryloxy)methyl)oxirane, 2,3-Epoxypropyl methacrylate, Methacrylic acid 2,3-epoxypropyl ester
Empirical Formula (Hill Notation):
C7H10O3
CAS Number:
106-91-2
Molecular Weight:
142.15
Beilstein:
2506
MDL number:
MFCD00005137
NACRES:
NA.21

grade

for synthesis

Quality Level

200

vapor pressure

4.2 hPa ( 25 °C)

refractive index

n20/D 1.449 (lit.)

bp

189 °C (lit.)

mp

<-60 °C

density

1.042 g/mL at 25 °C (lit.)
1.07 g/cm3 at 25 °C

SMILES string

CC(=C)C(=O)OCC1CO1

InChI

1S/C7H10O3/c1-5(2)7(8)10-4-6-3-9-6/h6H,1,3-4H2,2H3

InChI key

VOZRXNHHFUQHIL-UHFFFAOYSA-N

General description

2,3-Epoxypropyl methacrylate is a methacrylic acid/glycidol ester. It is used as a monomer to produce polymers based on glycidyl methacrylate (GMA). It is also a dual functionality (epoxy and methacrylate) monomer, thus offering the opportunity for chemical modification of the parent polymer for various applications.

Application

2,3-Epoxypropyl methacrylate can be used as a monomer unit in polymer industries to produce poly (glycidyl methacrylate)(PGMA) for various uses in electronic and biomedical applications. The presence of epoxide group in PGMA allows it to be modified by a variety of functionalities such as amine-epoxy, thiol-epoxy, azide-epoxy, and acid-epoxy via nucleophilic ring-opening reactions. This overall flexibility in the functionalization of PGMA is because of the controlled polymerization of 2,3-epoxypropyl methacrylate monomer via free radical polymerization. Thus, PGMA is one of the most adaptable reactive scaffolds in polymer chemistry due to the long shelf life of the resulting polymers.

It is also used to prepare poly(n-butyl methacrylate-co-glycidyl methacrylate) copolymers, which find applications in adhesives, surface coatings, and electrical devices in various polymeric industries. The presence of epoxy groups and flexible butyl groups in epoxy resin-modified copolymers increases its mechanical properties, impact strength, and fracture elongation.

Legal Information

Technipur is a registered trademark of Merck KGaA, Darmstadt, Germany

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 4 Oral - Carc. 1B - Eye Dam. 1 - Muta. 2 - Repr. 1B - Skin Corr. 1C - Skin Sens. 1 - STOT RE 1 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

168.8 °F - closed cup

Flash Point(C)

76 °C - closed cup

Regulatory Information

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Self-assembly and applications of poly(glycidyl methacrylate)s and their derivatives
Li Q-L, et al.
Chemical Communications (Cambridge, England), 87 (2014)
Diblock copolymers, triblock copolymers andmodel networks synthesized by sequential anionic polymerization of styrene and 2,3-epoxypropyl methacrylate
Hild G and Lamps J-P
Polymer, 39(12), 2637-2649 (1998)
Post-polymerization modification reactions of poly(glycidyl methacrylate)s
Muzammil EM, et al.
Royal Society of Chemistry Advances, 7, 55874-55884 (2017)
Shi G, et al.
Polymer-Plastics Technology and Engineering, 54(9), 881-888 (2015)
Epoxy-functional thermoplastic copolymers and their incorporation into a thermosetting resin
Sweet KR, et al.
Journal of Applied Polymer Science, 138(26), 50608-50608 (2021)

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