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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.
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.
Hazard Statements: H227-H302-H332
Combustible liquid. Harmful if swallowed. Harmful if inhaled.
Precautionary Statements: P210-P261-P264b-P270-P271-P280-P301+P312-P304+P340-P312-P330-P370+P378q-P501c
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Rinse mouth. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant