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Thermo Scientific Chemicals
Diphenyliodonium chloride, 98+%
CAS: 1483-72-3 | C12H10ClI | 316.57 g/mol
化学物質識別子
CAS1483-72-3
仕様
スペックシート
スペックシートAppearance (Color)White to cream
Assay (Titration ex Chloride)≥98.0 to ≤102.0%
Identification (FTIR)Conforms
FormCrystals or powder or crystalline powder
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.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Applications
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.
Solubility
Soluble in water and methanol.
Notes
Light sensitive. Incompatible with strong oxidizing agents.
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.
Solubility
Soluble in water and methanol.
Notes
Light sensitive. Incompatible with strong oxidizing agents.
RUO – Research Use Only
General References:
- 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.