Iodobenzene

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Iodobenzene
Iodobenzene Iodbenzol.svg
Iodobenzene
Iodobenzene-3D-vdW.png
Names
Preferred IUPAC name
Iodobenzene
Other names
Phenyl iodide
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.008.837 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C6H5I/c7-6-4-2-1-3-5-6/h1-5H Yes check.svgY
    Key: SNHMUERNLJLMHN-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C6H5I/c7-6-4-2-1-3-5-6/h1-5H
    Key: SNHMUERNLJLMHN-UHFFFAOYAQ
  • c1ccc(cc1)I
Properties
C6H5I
Molar mass 204.01 g/mol
Appearancecolorless liquid
Density 1.823 g/cm3
Melting point −29 °C (−20 °F; 244 K)
Boiling point 188 °C (370 °F; 461 K)
Insoluble
log P 3
−92.00·10−6 cm3/mol
Viscosity 1.5042 mPa·s (300.65 K) [1]
Hazards
Flash point 74.44 °C (165.99 °F; 347.59 K)
Thermochemistry
0.779 J/K
Related compounds
Related halobenzenes
 Fluorobenzene
Chlorobenzene
Bromobenzene
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Iodobenzene is an aryl iodide and the simplest of the iodobenzenes, consisting of a benzene ring substituted with one iodine atom. Its chemical formula is C6H5I. It is useful as a synthetic intermediate in organic chemistry. It is a volatile colorless liquid, although aged samples appear yellowish.

Contents

Preparation

Iodobenzene is commercially available, or it can be prepared in the laboratory from aniline via the diazotization reaction. In the first step, the amine functional group is diazotized with hydrochloric acid and sodium nitrite. Potassium iodide is added to the resultant phenyldiazonium chloride, causing nitrogen gas to evolve. The product is separated by steam distillation. [2]

Synthesis Iodobenzene.svg

Alternatively, it can be produced by refluxing iodine and nitric acid with benzene. [3]

Reactions

Since the C–I bond is weaker than C–Br or C–Cl, iodobenzene is more reactive than bromobenzene or chlorobenzene. Iodobenzene reacts readily with magnesium to form the Grignard reagent, phenylmagnesium iodide. Phenylmagnesium iodide, like the bromide analog, is a synthetic equivalent for the phenyl anion synthon. Iodobenzene reacts with chlorine to give the complex, iodobenzene dichloride, [4] which is used as a solid source of chlorine.

Iodobenzene can also serve as a substrate for the Sonogashira coupling, Heck reaction, and other metal-catalyzed couplings. These reactions proceed via the oxidative addition of iodobenzene.

Further reading

References

  1. ↑ Viswanath, D.S.; Natarajan, G. (1989), Data Book on the Viscosity of Liquids, Hemisphere Publishing, ISBN   0-89116-778-1
  2. ↑ H. J. Lucas, E. R. Kennedy (1939). "Iodobenzene". Organic Syntheses ; Collected Volumes, vol. 2, p. 351.
  3. ↑ F. B. Dains and R. Q. Brewster (1941). "Iodobenzene". Organic Syntheses ; Collected Volumes, vol. 1, p. 323.
  4. ↑ H. J. Lucas and E. R. Kennedy. "Iodobenzene dichloride". Organic Syntheses ; Collected Volumes, vol. 3, p. 482.
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