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Phenyl vinyl sulfone is used as building blocks in the synthesis of a number of organic substances, participate in polymerization reactions, nucleophilic addition reaction, and in cycloaddition reactions. It is also used in the used in the synthesis of reactive dyes, synthesis of textile fibers, in particular cellulose fibers such as cotton and linen. Other applications in the field of medicine includes as powerful inhibitors of certain enzymatic processes. It is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dye stuff.
Franklin A. Davis.; Sankar G. Lal.; H. Dupont Durst. Chemistry of oxaziridines. 10. Selective catalytic oxidation of sulfides to sulfoxides using N-sulfonyloxaziridines. J. Org. Chem. 1988, 53, (21), 5004-5007.K Grela .; M Bieniek. Highly selective cross-metathesis with phenyl vinyl sulphone using the 'second generation'Grubbs' catalyst. Tetrahedron Letters. 2001, 42, (36), 6425-6428.
Reactive dienophile. Can function as an acetylene equivalent if benzenesulfinic acid is eliminated thermally from the Diels-Alder adduct to form an olefinic double bond: J. Am. Chem. Soc., 100, 1597 (1978).
Can also behave as an activated form of ethylene if the sulfone group is cleaved from the adduct, e.g. with Na amalgam, with the possibility of prior alkylation of the adduct: J. Org. Chem., 48, 4976 (1983):
For addition to 1-Methoxy-3-trimethylsiloxy-1,3-butadiene, L06100, see: J. Org. Chem., 48, 4986 (1983). Addition to steroids with a cyclopentadienoid D-ring, followed by cleavage of the resulting alkene, gives the diformyl derivatives, useful for further functionalization: J. Chem. Soc., Perkin 1, 241 (1990).
For use in a 1,3-dipolar cycloaddition reaction, see 3-Hydroxypyridine, A13910.
Undergoes the Baylis-Hillman reaction (addition to aldehydes in the presence of 1,4-Diazabicyclo[2.2.2]octane, A14003): Tetrahedron, 44, 6095 (1988).
See also Divinyl sulfone, L12827.
Hazard Statements: H302-H315-H317-H318-H335
Harmful if swallowed. Causes skin irritation. May cause an allergic skin reaction. Causes serious eye damage. May cause respiratory irritation.
Precautionary Statements: P261-P264b-P270-P271-P272-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P310-P312-P330-P333+P313-P362-P501c
Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Contaminated work clothing should not be allowed out of the workplace. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician. Rinse mouth. If skin irritation or rash occurs: Get medical advice/attention. Take off contaminated clothing and wash before reuse. Dispose of contents/ container to an approved waste disposal plant