4-Iodophenol

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4-Iodophenol
4-Iodophenol.svg
4-Iodophenol powder.jpg
Names
IUPAC name
4-Iodophenol
Other names
    • p-Iodophenol
    • para-Iodophenol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.007.951 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 208-745-5
PubChem CID
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
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:
GHS-pictogram-exclam.svg GHS-pictogram-acid.svg [3]
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).

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

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Iodine monochloride is an interhalogen compound with the formula ICl. It is a red-brown chemical compound that melts near room temperature. Because of the difference in the electronegativity of iodine and chlorine, this molecule is highly polar and behaves as a source of I+. Discovered in 1814 by Gay-Lussac, iodine monochloride is the first interhalogen compound discovered.

<span class="mw-page-title-main">4-Aminophenol</span> Chemical compound

4-Aminophenol (or para-aminophenol or p-aminophenol) is an organic compound with the formula H2NC6H4OH. Typically available as a white powder, it is commonly used as a developer for black-and-white film, marketed under the name Rodinal.

4-Chlorophenol is an organic compound with the formula C6H4ClOH. It is one of three monochlorophenol isomers. It is a colorless or white solid that melts easily and exhibits significant solubility in water. Its pKa is 9.14.

Europium(III) iodide is an inorganic compound containing europium and iodine with the chemical formula EuI3.

<span class="mw-page-title-main">2-Iodophenol</span> 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.

<span class="mw-page-title-main">3-Iodophenol</span> Chemical compound

3-Iodophenol (m-iodophenol) is an aromatic organic compound. 3-Iodophenol participates in a variety of coupling reactions in which the iodide substituent is displaced. Well cited examples include thiolate and amine nucleophiles.

<span class="mw-page-title-main">Hafnium(III) iodide</span> Chemical compound

Hafnium(III) iodide is an inorganic compound of hafnium and iodine with the formula Hf I3. It is a black solid.

<span class="mw-page-title-main">Tungsten(II) iodide</span> Chemical compound

Tungsten(II) iodide is an iodide of tungsten, with the chemical formula [W6I8]I4, or abbreviated as WI2.

References

  1. 1 2 3 Haynes, p. 3.324
  2. Haynes, p. 5.93
  3. 1 2 "4-Iodophenol". Sigma-Aldrich.
  4. "4-Iodophenol". Fisher Scientific.
  5. Dains, F. B.; Eberly, Floyd (1935). "p-Iodophenol". Organic Syntheses. 15: 39. doi:10.15227/orgsyn.015.0039.

Cited sources