2-Iodophenol

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.^[3]

2-Iodophenol

Names
IUPAC name 2-Iodophenol
Other names o-Iodophenol ortho-Iodophenol
Identifiers
CAS Number	533-58-4 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:16706
ChEMBL	ChEMBL225564
ChemSpider	10328
ECHA InfoCard	100.007.792
EC Number	208-569-9
Gmelin Reference	406034
KEGG	C01874
PubChem CID	10784
UNII	F27L34A8B9
CompTox Dashboard (EPA)	DTXSID5052175
InChI InChI=1S/C6H5IO/c7-5-3-1-2-4-6(5)8/h1-4,8H Key: KQDJTBPASNJQFQ-UHFFFAOYSA-N
SMILES C1=CC=C(C(=C1)O)I
Properties
Chemical formula	C6H5IO
Molar mass	220.009 g·mol−1
Density	1.8757 g/cm3 (80 °C)[1]
Melting point	43 °C (109 °F; 316 K)[1]
Boiling point	186 °C (367 °F; 459 K)[1] (160 mmHg)
Acidity (pKa)	8.51[2]
Hazards
GHS labelling:
Pictograms	[3]
Hazard statements	H302, H312, H315, H319, H332, H335
Precautionary statements	P261, P280, P305+P351+P338
Related compounds
Related compounds	3-Iodophenol 4-Iodophenol 2-Fluorophenol 2-Chlorophenol 2-Bromophenol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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.^[4]