Iodobenzene

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title: "Iodobenzene" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["iodobenzenes", "phenyl-compounds"] topic_path: "general/iodobenzenes" source: "https://en.wikipedia.org/wiki/Iodobenzene" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

|Watchedfields = changed |verifiedrevid = 443876350 |Name = Iodobenzene |ImageFileL1 = Iodbenzol.svg |ImageSizeL1 = 80px |ImageNameL1 = Iodobenzene |ImageFileR1 = Iodobenzene-3D-vdW.png |ImageSizeR1 = 120px |ImageName1 = Space-filling model of iodobenzene |PIN = Iodobenzene |OtherNames = Phenyl iodide |Section1={{Chembox Identifiers |ChemSpiderID_Ref = |ChemSpiderID = 11087 |PubChem = 11575 |InChI = 1/C6H5I/c7-6-4-2-1-3-5-6/h1-5H |InChIKey = SNHMUERNLJLMHN-UHFFFAOYAQ |ChEMBL_Ref = |ChEMBL = 116296 |StdInChI_Ref = |StdInChI = 1S/C6H5I/c7-6-4-2-1-3-5-6/h1-5H |StdInChIKey_Ref = |StdInChIKey = SNHMUERNLJLMHN-UHFFFAOYSA-N |CASNo_Ref = |CASNo = 591-50-4 |UNII_Ref = |UNII = 9HK5L7YBBR |DrugBank_Ref = |DrugBank = DB02252 |SMILES = c1ccc(cc1)I |Section2={{Chembox Properties |Formula = C6H5I |Appearance = colorless liquid |MolarMass = 204.01 g/mol |Density = 1.823 g/cm3 |MeltingPtC = −29 |BoilingPtC = 188 |LogP = 3 |Solubility = Insoluble |MagSus = −92.00·10−6 cm3/mol |Viscosity = 1.5042 mPa·s (300.65 K) |Section3={{Chembox Hazards |FlashPtC = 74.44 |Section4={{Chembox Thermochemistry |HeatCapacity = 0.779 J/K |Section9={{Chembox Related | OtherFunction_label = halobenzenes | OtherFunction = Fluorobenzene Chlorobenzene Bromobenzene Astatobenzene

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 . 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.{{OrgSynth | author = H. J. Lucas, E. R. Kennedy | title = Iodobenzene | year = 1939 | collvol = 2 | collvolpages = 351 | prep = cv2p0351

:[[File:Synthesis Iodobenzene.svg|240px|Sandmeyer-Reaction]]

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

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, 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.

References

References

  1. (1989). "Data Book on the Viscosity of Liquids". Hemisphere Publishing.
  2. F. B. Dains and R. Q. Brewster. (1941). "Iodobenzene".
  3. H. J. Lucas and E. R. Kennedy. "Iodobenzene dichloride".

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iodobenzenesphenyl-compounds