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Diphenyliodonium chloride is used as a reagent for electrophilic phenylation . It is used as a reactant for copper-catalyzed cross coupling reactions of purinesband arylation of anilines. It is involved in the preparation of acetylenic arylselenide and (arylmethylene)oxindoles. Further, it is employed in the preparation of aryl alkynes through Sonogashira coupling reactions.
Diphenyliodonium salts are widely used as photoinitiators for cationic polymerization: Macromolecules, 10, 1307 (1977); review: Adv. Polym. Sci., 62, 1 (1982).
They are also useful phenylating agents for a variety of anions:
C-Phenylation of the anions derived from malonic esters, ß-keto esters and arylacetic esters: J. Org. Chem., 28, 714 (1963). Arylation of ketones: J. Org. Chem., 31, 4315 (1966). ß-Diketones can be arylated either as monoanions: Tetrahedron, 8, 49 (1960); J. Am. Chem. Soc., 84, 2819 (1962), or as dianions: J. Org. Chem., 29, 3514 (1964), where reaction occurs at the more reactive (terminal) carbon; see, e.g. (1-phenylation of 2,4-pentanedione): Org. Synth. Coll., 6, 928 (1988). For arylation of Grignard reagents and cyanide ion, see: J. Am. Chem. Soc., 75, 2708 (1953), and of nitro-compounds: J. Org. Chem., 28, 1424 (1963); 29, 2108 (1964). Other reactions reported include: O-Phenylation of aryloxides: J. Chem. Soc., 2645 (1961), alkoxides and oximes: J. Org. Chem., 40, 3010 (1975); 36, 1780 (1971); S-Phenylation of sulfides: J. Org. Chem., 36, 233 (1971); N-Phenylation of heterocycles: Tetrahedron, 1, 145 (1957); J. Org. Chem., 39, 2710 (1974).
For reviews of polyvalent iodine compounds in organic synthesis, see: Synthesis, 709 (1984); Chem. Rev., 96, 1123 (1996). For monographs, see: A. Varvoglis, The Organic Chemistry of Polycoordinated Iodine, VCH, N.Y. (1992); A. Varvoglis, Hypervalent Iodine in Organic Synthesis, Academic Press, San Diego (1996).
Kabatc, J.; Kostrzewska, K.; Dobosz, R.; Orzeł, Ł. Double role of squarylium dye: Fluorescence probe for biomolecule determination and photosensitizer in dyeing photoinitiating system. J. Mol. Liq. 2015, 212, 196-202.
Cook, W. D.; Chen, F. Enhanced visible radiation photopolymerization of dimethacrylates with the three component thioxanthone (CPTXO)-amine-iodonium salt system. Polym. Chem. 2015, 6 (8), 1325-1338.
Hazard Statements: H301-H315-H319-H335-H500
Toxic if swallowed. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation. May form combustible dust concentrations in air
Precautionary Statements: P261-P264b-P270-P271-P280-P301+P310-P302+P352-P304+P340-P305+P351+P338-P312-P330-P332+P313-P337+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. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. 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. Call a POISON CENTER or doctor/physician if you feel unwell. Rinse mouth. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse. Dispose of contents/ container to an approved waste disposal plant