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591-50-4 - Iodobenzene, 98% - A12788 - Alfa Aesar

A12788 Iodobenzene, 98%

CAS-Nummer
591-50-4
Synonyme

Größe Preis ($) Menge Verfügbarkeit
50g 38,49
100g 61,80
1000g 272,80
Zum Warenkorb hinzufügen Zur Angebotsanfrage hinzufügen Artikel anzeigen

Iodobenzene, 98%

MDL
MFCD00001029
EINECS
209-719-6

Chemische Eigenschaften

Formel
C6H5I
Molmasse
204.01
Schmelzpunkt
-31°
Siedepunkt
188-189°
Flammpunkt
74°(165°F)
Dichte
1.826
Brechungsindex
1.6200
Sensitivität
Light Sensitive
Löslichkeit
Miscible with ethanol, chloroform and ether. Slightly miscible with dimethyl sulfoxide. Immiscible with water.

Anwendungen

Iodobenzene is used to prepare biphenyl and stilbene. It reacts with magnesium to form the Grignard reagent, a phenylmagnesium iodide used in organic synthesis. It finds application as a solid chlorine source by reacting with chlorine to form a complex, iodobenzene dichloride. It serves as a substrate in Sonogashira reaction which is used to form a carbon-carbon bond between a terminal alkyne and an aryl halide.

Bemerkungen

Light sensitive. Incompatible with magnesium and strong oxidizing agents.

Literaturverweise

Active methylene compounds undergo CuI-catalyzed phenylation in DMSO: J. Org. Chem., 58, 7606 (1993).

In the presence of Pd catalysts, couples with a wide range of acrylic species or allylic alcohols in the Heck reaction. For example (2-methyl-2-propen-1-ol), see: Org. Synth. Coll., 7, 361 (1990).

For an extensive collection of the synthetically-useful reactions of iodoaromatics, see: Synthesis, 923 (1988).

Alla, S. K.; Kumar, R. K.; Sadhu, P.; Punniyamurthy, T. Iodobenzene Catalyzed C-H Amination of N-Substituted Amidines Using m-Chloroperbenzoic Acid. Org. Lett. 2013, 15 (6), 1334-1337.

Kurbangalieva, A.; Carmichael, D.; Hii, K. K.; Jutand, A.; Brown, J. M. Oxidative Addition to Palladium (0) Diphosphine Complexes: Observations of Mechanistic Complexity with Iodobenzene as Reactant. Chem. Eur. J. 2014, 20 (4), 1116-1125.

GHS Gefahren- und Sicherheitshinweise

Gefahrenhinweise (EU): H302

Harmful if swallowed.

Sicherheitshinweise: P261-P280f

Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective clothing.

Weitere Referenzen

Merck
14,5029
Beilstein
1446140
Harmonized Tariff Code
2903.99
TSCA
Yes
RTECS
DA3390000

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