Iodobenzene
5120016
221624353
2008-06-25T10:05:04Z
Arakin
142650
+ja
{{Chembox new
| Name = Iodobenzene
| ImageFileL1 = Iodobenzene.gif
| ImageSizeL1 = 100px
| ImageNameL1 = Iodobenzene
| ImageFileR1 = Iodobenzene-3D-vdW.png
| ImageSizeR1 = 120px
| ImageName1 = Space-filling model of iodobenzene
| IUPACName = Iodobenzene
| Section1 = {{Chembox Identifiers
| CASNo = 591-50-4
| SMILES = Ic1ccccc1
}}
| Section2 = {{Chembox Properties
| Formula = C<sub>6</sub>H<sub>5</sub>I
| MolarMass = 204.01 g/mol
| Density = 1.831 g/cm<sup>3</sup>
| MeltingPt = -29 °C
| BoilingPt = 188 °C
}}
}}
'''Iodobenzene''' is an [[organic compound]] consisting of a [[benzene]] ring substitituted with one [[iodine]] atom. It is useful as a synthetic intermediate in [[organic chemistry]]. Since the C-I bond is weaker than C-Br or C-Cl, it is more reactive than [[bromobenzene]] or [[chlorobenzene]]. Iodobenzene can react with [[magnesium]] to form a [[Grignard reagent]], phenylmagnesium iodide. Phenylmagnesium iodide, like the [[phenylmagnesium bromide|bromide]] analog, is a synthetic equivalent for the [[phenyl]] anion [[synthon]].
It can also serve as a [[substrate]] for the [[Sonogashira coupling]], [[Heck reaction]], and other metal-catalyzed couplings.
==Preparation==
Iodobenzene is commercially available, but it may be prepared in the laboratory from [[aniline]]. In the first step, the [[amine]] functional group is [[diazonium salt|diazotized]] with [[hydrochloric acid]] and [[sodium nitrite]]. [[Potassium iodide]] is added to the resultant diazonium chloride, causing [[nitrogen]] gas to evolve. Any excess nitrite is hydrolyzed with a strong base; the mixture is acidified and the desired product is separated by steam distillation.<ref>{{OrgSynth
| author = H. J. Lucas, E. R. Kennedy
| title = Iodobenzene
| year= 1939
| collvol = 2
| collvolpages = 351
| prep = cv2p0351
}}
</ref>
Alternatively, it may be produced by refluxing [[iodine]] and [[nitric acid]] with benzene.
<ref>{{OrgSynth
| author = F. B. Dains and R. Q. Brewster
| title = Iodobenzene
| year= 1941
| collvol = 1
| collvolpages = 323
| prep = cv1p323
}}
</ref>
==References==
<references/>
==See also==
*Gattermann-Wieland, "Laboratory Methods of Organic Chemistry," p. 283. Translated from the twenty-fourth German edition by W. McCartney, The Macmillan Company, New York, 1937.
[[Category:Aromatic compounds]]
[[Category:Organoiodides]]
[[ja:ヨードベンゼン]]