2-Iodophenol

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2-Iodophenol
2-Iodophenol.svg
Names
IUPAC name
2-Iodophenol
Other names
    • o-Iodophenol
    • ortho-Iodophenol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.792 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 208-569-9
406034
KEGG
PubChem CID
UNII
  • InChI=1S/C6H5IO/c7-5-3-1-2-4-6(5)8/h1-4,8H
    Key: KQDJTBPASNJQFQ-UHFFFAOYSA-N
  • C1=CC=C(C(=C1)O)I
Properties
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:
GHS-pictogram-exclam.svg [3]
H302, H312, H315, H319, H332, H335
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 [77 °F], 100 kPa).

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]

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]

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<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.

<span class="mw-page-title-main">Mercury(I) fluoride</span> Chemical compound

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

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An iodophenol is any organoiodide of phenol that contains one or more covalently bonded iodine atoms. There are five basic types of iodophenols and 19 different iodophenols in total when positional isomerism is taken into account. Iodophenols are produced by electrophilic halogenation of phenol with iodine.

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

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

<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.

References

  1. 1 2 3 Haynes, p. 3.324
  2. Haynes, p. 5.93
  3. 1 2 "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