4-Iodophenol

4-Iodophenol (p-iodophenol) is an aromatic organic compound. A colorless solid, it is one of three monoiodophenols. 4-Iodophenol undergoes a variety of coupling reactions in which the iodine substituent is replaced by a new carbon group para to the hydroxy group of the phenol.^[3] It is also used to enhance chemiluminescence for detection of cancer cells^[4] and in the Eclox assay.

4-Iodophenol

Names
IUPAC name 4-Iodophenol
Other names p-Iodophenol para-Iodophenol
Identifiers
CAS Number	540-38-5 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:43521
ChEMBL	ChEMBL56475
ChemSpider	10432
DrugBank	DB03002
ECHA InfoCard	100.007.951
EC Number	208-745-5
PubChem CID	10894
UNII	BH194BAK0B
CompTox Dashboard (EPA)	DTXSID4052186
InChI InChI=1S/C6H5IO/c7-5-1-3-6(8)4-2-5/h1-4,8H Key: VSMDINRNYYEDRN-UHFFFAOYSA-N
SMILES C1=CC(=CC=C1O)I
Properties
Chemical formula	C6H5IO
Molar mass	220.009 g·mol−1
Density	1.8573 g/cm3 (112 °C)[1]
Melting point	93.5 °C (200.3 °F; 366.6 K)[1]
Boiling point	139 °C (282 °F; 412 K)[1] (5 mmHg; decomposes)
Acidity (pKa)	9.33[2]
Hazards
GHS labelling:
Pictograms	[3]
Hazard statements	H302, H312, H314
Precautionary statements	P280, P305+P351+P338, P310
Related compounds
Related compounds	2-Iodophenol 3-Iodophenol 4-Fluorophenol 4-Chlorophenol 4-Bromophenol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

4-Iodophenol can be prepared from 4-aminophenol via the diazonium salt. An alternative synthesis involves reaction of salicylic acid with iodine, followed by decarboxylation.^[5]