Cas no 3555-94-0 (isocyanatoethene)

Isocyanatoethene, also known as vinyl isocyanate, is a highly reactive monomer with the chemical formula C?H?NO. It features an isocyanate group (–NCO) bonded to an ethene (vinyl) moiety, enabling its use in polymerization and cross-linking reactions. This compound is particularly valued in specialty polymer synthesis, where it contributes to the formation of polyurethane and polyurea derivatives with tailored properties. Its reactivity allows for efficient incorporation into copolymers, enhancing material durability and chemical resistance. Due to its volatility and toxicity, handling requires strict safety measures, including proper ventilation and personal protective equipment. Isocyanatoethene is primarily utilized in research and industrial applications requiring precise functional group reactivity.
isocyanatoethene structure
isocyanatoethene structure
Product Name:isocyanatoethene
CAS No:3555-94-0
MF:C3H3NO
MW:69.0620205402374
CID:312207
PubChem ID:77094
Update Time:2025-06-09

isocyanatoethene Chemical and Physical Properties

Names and Identifiers

    • Vinyl isocyanate
    • Ethene, isocyanato-(9CI)
    • isocyanatoethene
    • 531618_ALDRICH
    • AC1L2SCL
    • AC1Q6BKS
    • Acrylic isocyanate
    • CTK4H4796
    • Ethene, isocyanato-
    • isocyanic acid vinyl ester
    • N-vinylisocyanate
    • Vinylisocyanat
    • Vinyl isocyanate, 95%
    • WARQUFORVQESFF-UHFFFAOYSA-N
    • 3555-94-0
    • DTXSID40189040
    • VINYL ISOCYANATE 97
    • EINECS 222-616-0
    • NS00029875
    • CH2=CHNCO
    • EN300-141417
    • Inchi: 1S/C3H3NO/c1-2-4-3-5/h2H,1H2
    • InChI Key: WARQUFORVQESFF-UHFFFAOYSA-N
    • SMILES: O=C=NC=C

Computed Properties

  • Exact Mass: 69.02149
  • Monoisotopic Mass: 69.021463719g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 5
  • Rotatable Bond Count: 1
  • Complexity: 71
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Surface Charge: 0
  • Tautomer Count: nothing
  • XLogP3: 1.7
  • Topological Polar Surface Area: 29.4?2

Experimental Properties

  • Color/Form: Not determined
  • Density: 0.938?g/mL?at 25?°C(lit.)
  • Boiling Point: 39-40?°C(lit.)
  • Flash Point: 40?°F
  • Refractive Index: n20/D 1.4190(lit.)
  • PSA: 29.43
  • LogP: 0.46570
  • Solubility: Not determined

isocyanatoethene Security Information

isocyanatoethene Pricemore >>

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Additional information on isocyanatoethene

Introduction to Isocyanatoethene (CAS No. 3555-94-0)

Isocyanatoethene, with the chemical formula C?H?NO? and a CAS number of 3555-94-0, is a significant compound in the field of organic chemistry and industrial applications. This versatile molecule, characterized by its highly reactive isocyanate functional group, has garnered considerable attention due to its role in synthesizing various high-value chemicals. The unique structural and chemical properties of isocyanatoethene make it a crucial intermediate in the production of polymers, pharmaceuticals, and specialty materials.

The isocyanate functional group in isocyanatoethene (–N=C=O) is known for its ability to participate in a wide range of chemical reactions, including polymerization, condensation, and addition reactions. This reactivity has positioned isocyanatoethene as a key building block in the synthesis of polyurethanes, which are widely used in coatings, adhesives, foams, and elastomers. The compound's ability to form stable bonds with hydroxyl groups has made it indispensable in the production of flexible and rigid polyurethane foams used in automotive, construction, and packaging industries.

In recent years, research into isocyanatoethene has expanded beyond traditional polymer chemistry into more specialized applications. One notable area is its use in the development of novel pharmaceuticals. The reactivity of the isocyanate group allows for the formation of biologically active molecules through condensation reactions with amines and alcohols. This property has been exploited in the synthesis of protease inhibitors and other therapeutic agents where precise molecular architecture is critical for biological activity.

Moreover, advancements in green chemistry have prompted investigations into more sustainable methods for producing isocyanatoethene. Traditional synthesis routes often involve hazardous conditions and byproducts that are challenging to manage environmentally. Researchers are now exploring catalytic processes that minimize waste and reduce energy consumption while maintaining high yields of isocyanatoethene. These efforts align with global initiatives to develop greener alternatives for industrial chemicals.

The role of isocyanatoethene in material science has also seen significant developments. Researchers have leveraged its reactivity to create advanced materials with tailored properties. For instance, functionalized polyurethanes derived from isocyanatoethene have been developed for applications requiring enhanced durability, thermal stability, or biodegradability. These materials are particularly relevant in industries seeking sustainable solutions without compromising performance.

Another emerging application of isocyanatoethene is in the field of nanotechnology. The compound's ability to form stable monolayers on surfaces has made it useful for modifying substrate properties at the nanoscale. This has implications for improving surface wettability, adhesion, and corrosion resistance in various industrial applications. The precision with which isocyanatoethene can modify surface chemistry makes it a valuable tool for researchers developing next-generation materials.

The pharmaceutical industry continues to explore new derivatives of isocyanatoethene for drug development. By incorporating this moiety into molecular structures, researchers can enhance drug bioavailability and target specificity. Recent studies have shown promising results in using isocyanatoethene-based compounds as prodrugs or drug carriers, which can improve therapeutic efficacy while reducing side effects.

In conclusion, Isocyanatoethene (CAS No. 3555-94-0) remains a pivotal compound in modern chemistry due to its diverse applications across multiple industries. From traditional polymer manufacturing to cutting-edge pharmaceuticals and nanotechnology, the reactivity and versatility of this molecule continue to drive innovation. As research progresses, it is expected that new applications for isocyanatoethene will emerge, further solidifying its importance in scientific and industrial landscapes worldwide.

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