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Nitroethylene also known as nitroethene is a liquid organic compound with the formula C 2 H 3 NO 2. It is the simplest nitroalkene , which are unsaturated carbon chains with at least one double bond and a NO 2 functional group. Nitroethylene serves as a useful intermediate in the production of various other chemicals. Nitroethylene has a dipole moment from the electron withdrawing nitro group present in the molecule, even though it is a neutral species. As a result, it is soluble in water and non-polar solvents. Nitroethylene is extremely reactive, even at low temperatures. It readily decomposes at room temperature. Nitroethene can be produced by reacting nitromethane with formaldehyde or paraformaldehyde a polymeric form to form 2-nitroethanol, which can then undergo an E2 acid-catalyzed dehydration reaction. Nitroethylene is a very electron deficient molecule. As a result, nitroethylene usually acts as the electrophile in reactions. Common reactions for this molecule are cycloadditions, radical additions, and nucleophilic additions. The nitro group in the molecule serves as an electron withdrawing group that makes the molecule a good candidate as a dienophile. Nitroethylene is also reactive in domino-cycloaddition processes. At very low temperatures i. This process can be moderated by using t-butyl solvent. Research has been conducted on performing batch polymerization at room temperature in THF solvent. This process requires gamma ray irradiation for initiation. Termination of the polymerization requires a radical retardant, such as hydrogen bromide or hydrogen chloride. Water must be carefully removed prior to the polymerization, as nitroethylene is sensitive to polymerization by traces of water. A typical Michael donor i. Another example is the Michael reaction of indole and nitroethylene. The main use of nitroethylene is as an intermediate reagent in chemical synthesis. One example is the production of N- 2-nitroethyl -aniline with aniline at room temperature. Another example of nitroethylene is from the coupling reaction with a vinyl Grignard reagent and a silyl glyoxalate to form a nitrocylopentanol. This process via a Henry reaction and is highly diastereoselective. From Wikipedia, the free encyclopedia. CAS Number. Interactive image. Beilstein Reference. PubChem CID. Chemical formula. Solubility in water. Heat capacity C. Std molar entropy S o K; Iyengar, R. Radiation-Induced Polymerization of Nitroethylene. Faraday Soc. DOI: The Journal of Organic Chemistry. College Station: n. Wiley Online Library. Chemistry of Heterocyclic Compounds. Collection of Czechoslovak Chemical Communications. Chi, L. Guo, N. Kopf, S. Angewandte Chemie International Edition , , 49 47 , pp. Categories : Nitro compounds Alkene derivatives Vinyl compounds. Namespaces Article Talk. Views Read Edit View history. By using this site, you agree to the Terms of Use and Privacy Policy. IUPAC name 1-nitroethene. External MSDS.