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.[1] It is also used to enhance chemiluminescence for detection of cancer cells[2] and in the Eclox assay.

4-Iodophenol
Names
IUPAC name
4-Iodophenol
Other names
    • p-Iodophenol
    • para-Iodophenol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.007.951
EC Number
  • 208-745-5
UNII
  • InChI=1S/C6H5IO/c7-5-1-3-6(8)4-2-5/h1-4,8H
    Key: VSMDINRNYYEDRN-UHFFFAOYSA-N
  • C1=CC(=CC=C1O)I
Properties
C6H5IO
Molar mass 220.009 g·mol−1
Melting point 42–44 °C (108–111 °F; 315–317 K)[1]
Boiling point 138 °C (280 °F; 411 K)[2] (5 mmHg)
Acidity (pKa) 9.20[3]
Hazards
GHS labelling:
GHS07: Exclamation markGHS05: Corrosive[1]
H302, H312, H314
P280, P305+P351+P338, P310
Related compounds
Related compounds
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.[4]

References
  1. "4-Iodophenol". Sigma-Aldrich.
  2. "4-Iodophenol". Fisher Scientific.
  3. Rappoport (1984). CRC Handbook of Tables for Organic Compound Identification (3rd ed.). ISBN 0-8493-0303-6.
  4. F. B. Dains, Floyd Eberly (1935). "p-Iodophenol". Organic Syntheses. 15: 39. doi:10.15227/orgsyn.015.0039.
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