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477060

Sigma-Aldrich

2-Isocyanatoethyl methacrylate

contains ≤0.1% BHT as inhibitor, 98%

Synonym(s):

2-(Methacryloyloxy)ethyl isocyanate, IEM

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About This Item

Linear Formula:
H2C=C(CH3)CO2CH2CH2NCO
CAS Number:
Molecular Weight:
155.15
EC Number:
MDL number:
UNSPSC Code:
12162002
PubChem Substance ID:
NACRES:
NA.23

Quality Level

Assay

98%

contains

≤0.1% BHT as inhibitor

refractive index

n20/D 1.45 (lit.)

bp

211 °C (lit.)

mp

−45 °C (lit.)

density

1.098 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

CC(=C)C(=O)OCCN=C=O

InChI

1S/C7H9NO3/c1-6(2)7(10)11-4-3-8-5-9/h1,3-4H2,2H3

InChI key

RBQRWNWVPQDTJJ-UHFFFAOYSA-N

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General description

2-Isocyanatoethyl methacrylate, belongs to the class of monomers known as isocyanate monomers. The presence of the isocyanate functional group in 2-Isocyanatoethyl methacrylate makes it highly reactive. This reactivity allows it to undergo polymerization and form cross-linked networks for the development of polymers with improved mechanical strength, chemical resistance, and adhesion properties. It is also used as a crosslinker in the manufacture of many resins, in electrodeposition, and adhesives, and as a co-monomer in crosslinked polymer polyolstyrene-acrylic resin, which is used in construction products, such as ceramic tile adhesives, fillers, putties, and elastomeric roof coatings.

Application

2-Isocyanatoethyl methacrylate can be used as:
  • A reactive monomer in the synthesis of poly(methyl urethane) acrylate oligomer for UV-curable coatings. By incorporating urethane and acrylate groups into the polymer, it enables the polymer to be utilized in UV-curable coatings, inks, and adhesives.
  • An additive in propylene carbonate-based electrolyte to enhance its properties, such as viscosity, conductivity, and stability. This improves the overall performance of the electrolyte and the battery.
  • As a modifier in the copolymerization process to prepare a bioprosthetic heart valve, which is used in the application of transcatheter aortic valve replacement.
  • A latent cross-linker for adhesive resins and coatings.

Signal Word

Danger

Hazard Classifications

Acute Tox. 1 Inhalation - Acute Tox. 4 Oral - Eye Dam. 1 - Resp. Sens. 1 - Skin Irrit. 2 - Skin Sens. 1

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

210.2 °F - closed cup

Flash Point(C)

99 °C - closed cup


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T Furuzono et al.
Biomaterials, 21(4), 327-333 (2000-02-03)
2-Methacryloyloxyethyl phosphorylcholine (MPC) was grafted onto silk fabric in a two-step heterogeneous system through the vinyl bonds of 2-methacryloyloxyethyl isocyanate (MOI) modified on the fabric. First, habutae silk fabric was modified with the MOI monomer in anhydrous dimethyl sulfoxide using
Spec. Chem. Technol., 29, 765-765 (1984)
Christine Lehmann et al.
PLoS pathogens, 14(5), e1007031-e1007031 (2018-05-17)
Parasite egress from infected erythrocytes and invasion of new red blood cells are essential processes for the exponential asexual replication of the malaria parasite. These two tightly coordinated events take place in less than a minute and are in part
T Konno et al.
Biomaterials, 22(13), 1883-1889 (2001-06-09)
The poly(L-lactic acid) nanoparticles immobilized with 2-methacryloyloxyethyl phosphorylcholine (MPC) polymer, which has excellent blood compatibility, were prepared by a solvent evaporation technique using the water-soluble amphiphilic MPC polymer as an emulsifier and a surface modifier. The diameter and zeta-potential of
Mitsumasa Sudo et al.
Atherosclerosis, 265, 283-291 (2017-07-12)
Glucagon-like peptide-1 (GLP-1) is thought to inhibit development of aortic atherosclerosis and plaque formation. However, whether GLP-1 stabilizes fully developed atherosclerotic plaque or alters the complicated plaque composition remains unclarified. Ten Watanabe heritable hyperlipidemic (WHHL) rabbits were divided into GLP-1

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