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

A15149 Diphenyliodonium chloride, 98+%

Número CAS
1483-72-3
Nombre Alternativo

Tamaño Precio ($) Cantidad Disponibilidad
10g 71,40
50g 323,00
250g 1279,00
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Diphenyliodonium chloride, 98+%

MDL
MFCD00011909
EINECS
216-049-8

Propiedades químicas

Fórmula
C12H10ClI
Peso molecular
316.57
Punto de fusión
ca 230° dec.
Sensibilidad
Light Sensitive
Solubilidad
Soluble in water and methanol.

Aplicaciones

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.

Notas

Light sensitive. Incompatible with strong oxidizing agents.

Referencias documentales

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.

Indicaciones de peligro y de precaución del GHS

Indicaciones de peligro (UE): H301-H315-H319-H335

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

Indicaciones de precaución: 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.

Otras referencias

Merck
14,7464
Beilstein
3574977
Clase de peligro
6.1
Grupo de embalaje
III
Código de tarifa arancelaria unificado
2903.99
TSCA
Yes
RTECS
NN6651666

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