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

A15149 Diphenyliodonium chloride, 98+%

CAS-Nummer
1483-72-3
Synonyme

Größe Preis ($) Menge Verfügbarkeit
10g 72,10
50g 285,30
250g 1003,20
Zum Warenkorb hinzufügen Zur Angebotsanfrage hinzufügen Artikel anzeigen

Diphenyliodonium chloride, 98+%

MDL
MFCD00011909
EINECS
216-049-8

Chemische Eigenschaften

Formel
C12H10ClI
Molmasse
316.57
Schmelzpunkt
ca 230° dec.
Sensitivität
Light Sensitive
Löslichkeit
Soluble in water and methanol.

Anwendungen

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.

Bemerkungen

Light sensitive. Incompatible with strong oxidizing agents.

Literaturverweise

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.

GHS Gefahren- und Sicherheitshinweise

Gefahrenhinweise (EU): H301-H315-H319-H335

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

Sicherheitshinweise: P261-P280-P301+P310-P305+P351+P338-P304+P340-P362-P312-P405-P403+P233-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Take off contaminated clothing and wash before reuse. Call a POISON CENTER or doctor/physician if you feel unwell. Store locked up. Store in a well-ventilated place. Keep container tightly closed. Dispose of contents/container in accordance with local/regional/national/international regulations.

Weitere Referenzen

Merck
14,7464
Beilstein
3574977
Gefahrenklasse
6.1
Verpackungsgruppe
III
Harmonized Tariff Code
2903.99
TSCA
Yes
RTECS
NN6651666

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