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

A12788 Iodobenzene, 98%

CAS Number
591-50-4
Synonyms

Size Price ($) Quantity Availability
50g 38.49
100g 61.80
1000g 272.80
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Iodobenzene, 98%

MDL
MFCD00001029
EINECS
209-719-6

Chemical Properties

Formula
C6H5I
Formula Weight
204.01
Melting point
-31°
Boiling Point
188-189°
Flash Point
74°(165°F)
Density
1.826
Refractive Index
1.6200
Sensitivity
Light Sensitive
Solubility
Miscible with ethanol, chloroform and ether. Slightly miscible with dimethyl sulfoxide. Immiscible with water.

Applications

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.

Notes

Light sensitive. Incompatible with magnesium and strong oxidizing agents.

Literature References

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 Hazard and Precautionary Statements

Hazard Statements: H302

Harmful if swallowed.

Precautionary Statements: P261-P280f

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

Other References

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

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