Methacryloyloxyethyl isocyanate

Last updated
Methacryloyloxyethyl isocyanate
Methacryloyloxyethyl isocyanate.svg
Names
Preferred IUPAC name
2-Isocyanatoethyl 2-methylprop-2-enoate
Identifiers
  • 30674-80-7 Yes check.svgY
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.045.698 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 250-284-7
PubChem CID
UNII
  • InChI=1S/C7H9NO3/c1-6(2)7(10)11-4-3-8-5-9/h1,3-4H2,2H3
    Key: RBQRWNWVPQDTJJ-UHFFFAOYSA-N
  • InChI=1/C7H9NO3/c1-6(2)7(10)11-4-3-8-5-9/h1,3-4H2,2H3
    Key: RBQRWNWVPQDTJJ-UHFFFAOYAT
  • CC(=C)C(=O)OCCN=C=O
Properties
C7H9NO3
Molar mass 155.153 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Methacryloyloxyethyl isocyanate is an extremely poisonous liquid which can be fatal if inhaled, absorbed through skin, or consumed orally. To a lesser extent it can burn eyes and skin on contact. [1] It is used as a cross-linker in the production of synthetic resins.

Related Research Articles

Polyurethane Polymer composed of a chain of organic units joined by carbamate (urethane) links

Polyurethane is a polymer composed of organic units joined by carbamate (urethane) links. While most polyurethanes are thermosetting polymers that do not melt when heated, thermoplastic polyurethanes are also available.

Isocyanate

Isocyanate is the functional group with the formula R−N=C=O. Organic compounds that contain an isocyanate group are referred to as isocyanates. An organic compound with two isocyanate groups is known as a diisocyanate. Diisocyanates are manufactured for the production of polyurethanes, a class of polymers.

Methyl isocyanate Chemical compound

Methyl isocyanate (MIC) is an organic compound with the molecular formula CH3NCO. Synonyms are isocyanatomethane, methyl carbylamine and MIC. Methyl isocyanate is an intermediate chemical in the production of carbamate pesticides (such as carbaryl, carbofuran, methomyl, and aldicarb). It has also been used in the production of rubbers and adhesives. As a highly toxic and irritating material, it is extremely hazardous to human health. It was the principal toxicant involved in the Bhopal disaster, which killed 2,259 people initially and officially 20,000 people in total.

Thermosetting polymer

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Carbaryl Chemical compound

Carbaryl is a chemical in the carbamate family used chiefly as an insecticide. It is a white crystalline solid commonly sold under the brand name Sevin, a trademark of the Bayer Company. Union Carbide discovered carbaryl and introduced it commercially in 1958. Bayer purchased Aventis CropScience in 2002, a company that included Union Carbide pesticide operations. It remains the third-most-used insecticide in the United States for home gardens, commercial agriculture, and forestry and rangeland protection. As a veterinary drug, it is known as carbaril (INN).

Carbonless copy paper

Carbonless copy paper (CCP), non-carbon copy paper, or NCR paper is a type of coated paper designed to transfer information written on the front onto sheets beneath. It was developed by chemists Lowell Schleicher and Barry Green, as an alternative to carbon paper and is sometimes misidentified as such.

Polyurea Class of elastomers

Polyurea is a type of elastomer that is derived from the reaction product of an isocyanate component and a synthetic resin blend component through step-growth polymerization. The isocyanate can be aromatic or aliphatic in nature. It can be monomer, polymer, or any variant reaction of isocyanates, quasi-prepolymer or a prepolymer. The prepolymer, or quasi-prepolymer, can be made of an amine-terminated polymer resin, or a hydroxyl-terminated polymer resin.

The Hofmann rearrangement is the organic reaction of a primary amide to a primary amine with one fewer carbon atom. The reaction involves oxidation of the nitrogen followed by rearrangement of the carbonyl and nitrogen to give an isocyanate intermediate. The reaction can form a wide range of products, including alkyl and aryl amines.

Toluene diisocyanate Chemical compound

Toluene diisocyanate (TDI) is an organic compound with the formula CH3C6H3(NCO)2. Two of the six possible isomers are commercially important: 2,4-TDI (CAS: 584-84-9) and 2,6-TDI (CAS: 91-08-7). 2,4-TDI is produced in the pure state, but TDI is often marketed as 80/20 and 65/35 mixtures of the 2,4 and 2,6 isomers respectively. It is produced on a large scale, accounting for 34.1% of the global isocyanate market in 2000, second only to MDI. Approximately 1.4 billion kilograms were produced in 2000. All isomers of TDI are colorless, although commercial samples can appear yellow.

Cyanate

Cyanate is an anion with the structural formula [O=C=N], usually written OCN. It also refers to any salt containing it, such as ammonium cyanate.

Curtius rearrangement

The Curtius rearrangement, first defined by Theodor Curtius in 1885, is the thermal decomposition of an acyl azide to an isocyanate with loss of nitrogen gas. The isocyanate then undergoes attack by a variety of nucleophiles such as water, alcohols and amines, to yield a primary amine, carbamate or urea derivative respectively. Several reviews have been published.

Polyisocyanurate Type of plastic typically used for thermal insulation

Polyisocyanurate, also referred to as PIR, polyiso, or ISO, is a thermoset plastic typically produced as a foam and used as rigid thermal insulation. The starting materials are similar to those used in polyurethane (PUR) except that the proportion of methylene diphenyl diisocyanate (MDI) is higher and a polyester-derived polyol is used in the reaction instead of a polyether polyol. The resulting chemical structure is significantly different, with the isocyanate groups on the MDI trimerising to form isocyanurate groups which the polyols link together, giving a complex polymeric structure.

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Spray foam

Spray foam is a chemical product created by two materials, isocyanate and polyol resin, which react when mixed with each other and expand up to 30-60 times its liquid volume after it is sprayed in place. This expansion makes it useful as a specialty packing material which forms to the shape of the product being packaged and produces a high thermal insulating value with virtually no air infiltration.

Polypropylene polybenzyl isocyanate (PPI), is a polyurea-based polymer derived from isocyanate monomers that is used in some glues, aerosol foams, plastics, paint and household products.

Hydroxylammonium sulfate Chemical compound

Hydroxylammonium sulfate (NH3OH)2SO4, is the sulfuric acid salt of hydroxylamine. It is primarily used as an easily handled form of hydroxylamine, which is explosive when pure.

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T-1123 Chemical compound

T-1123 is a carbamate-based acetylcholinesterase inhibitor. It was investigated as a chemical warfare agent starting in 1940. It does not go through the blood-brain barrier due to the charge on quaternary nitrogen. The antidote is atropine. T-1123 is a quaternary ammonium ion. A phenyl carbamate ester is bonded in the meta position to the nitrogen on a diethylmethyl amine. The chloride and methylsulfate salt of T-1123 is TL-1299 and TL-1317, respectively.

References

  1. Methacryloyloxyethyl isocyanate at cameochemicals.noaa.gov.