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2-Iodophenol

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2-Iodophenol
Names
IUPAC name 2-Iodophenol
Other names
    • o-Iodophenol
    • ortho-Iodophenol
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.792 Edit this at Wikidata
EC Number
  • 208-569-9
Gmelin Reference 406034
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H5IO/c7-5-3-1-2-4-6(5)8/h1-4,8HKey: KQDJTBPASNJQFQ-UHFFFAOYSA-N
SMILES
  • C1=CC=C(C(=C1)O)I
Properties
Chemical formula C6H5IO
Molar mass 220.009 g·mol
Density 1.8757 g/cm (80 °C)
Melting point 43 °C (109 °F; 316 K)
Boiling point 186 °C (367 °F; 459 K) (160 mmHg)
Acidity (pKa) 8.51
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
Hazard statements H302, H312, H315, H319, H332, H335
Precautionary statements P261, P280, P305+P351+P338
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

2-Iodophenol (o-iodophenol) is an aromatic organic compound with the formula IC6H4OH. It is a pale yellow solid that melts near room temperature. It undergoes a variety of coupling reactions in which the iodine substituent is replaced by a new carbon group ortho to the hydroxy group of the phenol, which can be followed by cyclization to form heterocycles.

It can be prepared by treatment of 2-chloromercuriphenol with iodine:

ClHgC6H4OH + I2 → IC6H4OH + HgCl(I)

Direct reaction of phenol with iodine gives a mixture of 2- and 4-iodo derivatives.

References

  1. ^ Haynes, p. 3.324
  2. Haynes, p. 5.93
  3. ^ "2-Iodophenol". Sigma-Aldrich.
  4. Whitmore, F. C.; Hanson, E. R. (1925). "o-Iodophenol". Organic Syntheses. 4: 37. doi:10.15227/orgsyn.004.0037.

Cited sources

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