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1483-72-3 - Diphenyliodonium chloride, 98+% - A15149 - Alfa Aesar

A15149 Diphenyliodonium chloride, 98+%

Codice CAS
1483-72-3
Sinonimi

Dimensioni Prezzo ($) Quantità Disponibilità
10g 71,40
50g 323,00
250g 1279,00
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Diphenyliodonium chloride, 98+%

MDL
MFCD00011909
EINECS
216-049-8

Proprietà chimiche

Formula
C12H10ClI
Peso formula
316.57
Punto di fusione
ca 230° dec.
Sensibilità
Light Sensitive
Solubilità
Soluble in water and methanol.

Applicazioni

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.

Note

Light sensitive. Incompatible with strong oxidizing agents.

Letteratura

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.

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): H301-H315-H319-H335

Toxic if swallowed. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Dichiarazioni precauzionali: P261-P280a-P301+P310a-P305+P351+P338-P405-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves and eye/face protection. IF SWALLOWED: Immediately call a POISON CENTER/doctor IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Altri riferimenti

Merck
14,7464
Beilstein
3574977
Classe di rischio
6.1
Gruppo di imballaggio
III
Codice tariffe armonizzato
2903.99
TSCA
Yes
RTECS
NN6651666

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