Iodobenzene

Iodobenzene
Iodobenzene
Iodobenzene
Names
Preferred IUPAC name
Iodobenzene
Other names
Phenyl iodide
Identifiers
CAS Number
  • 591-50-4 checkY
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL116296 checkY
ChemSpider
  • 11087 checkY
DrugBank
  • DB02252 checkY
ECHA InfoCard 100.008.837 Edit this at Wikidata
PubChem CID
  • 11575
UNII
  • 9HK5L7YBBR checkY
CompTox Dashboard (EPA)
  • DTXSID8060452 Edit this at Wikidata
InChI
  • InChI=1S/C6H5I/c7-6-4-2-1-3-5-6/h1-5H checkY
    Key: SNHMUERNLJLMHN-UHFFFAOYSA-N checkY
  • InChI=1/C6H5I/c7-6-4-2-1-3-5-6/h1-5H
    Key: SNHMUERNLJLMHN-UHFFFAOYAQ
  • c1ccc(cc1)I
Properties
Chemical formula
C6H5I
Molar mass 204.01 g/mol
Appearance colorless liquid
Density 1.823 g/cm3
Melting point −29 °C (−20 °F; 244 K)
Boiling point 188 °C (370 °F; 461 K)
Solubility in water
Insoluble
log P 3
Magnetic susceptibility (χ)
-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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Infobox references
Chemical compound

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.

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]

Sandmeyer-Reaction

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

  • 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.

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.