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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:
30674-80-7
Molecular Weight:
155.15
EC Number:
250-284-7
MDL number:
MFCD00080536
UNSPSC Code:
12162002
PubChem Substance ID:
24871328
NACRES:
NA.23

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.

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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

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

wgk_germany

WGK 3

flash_point_f

210.2 °F - closed cup

flash_point_c

99 °C - closed cup

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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