2-Iodophenol

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|ImageFile = 2-Iodophenol.svg

|ImageSize = 120px

|IUPACName = 2-Iodophenol

|OtherNames = {{ubl|

• o-Iodophenol
• ortho-Iodophenol

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| Section1 = {{Chembox Identifiers

| CASNo = 533-58-4

| CASNo_Ref = {{cascite|correct|CAS}}

| ChEBI = 16706

| ChEMBL = 225564

| PubChem = 10784

| ChemSpiderID = 10328

| EC_number = 208-569-9

| Gmelin = 406034

| KEGG = C01874

| UNII = F27L34A8B9

| SMILES = C1=CC=C(C(=C1)O)I

| InChI = 1S/C6H5IO/c7-5-3-1-2-4-6(5)8/h1-4,8H

| InChIKey = KQDJTBPASNJQFQ-UHFFFAOYSA-N

}}

| Section2 = {{Chembox Properties

| C=6 | H=5 | I=1 | O=1

| Density = 1.8757 g/cm³ (80 °C)Haynes, p. 3.324

| MeltingPtC = 43

| MeltingPt_ref =

| BoilingPtC = 186

| BoilingPt_notes= (160 mmHg)

| BoilingPt_ref =

| pKa = 8.51Haynes, p. 5.93

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| Section3 = {{Chembox Hazards

| MainHazards =

| NFPA-H =

| NFPA-F =

| NFPA-I =

| NFPA-S =

| GHSPictograms = {{GHS exclamation mark}}

| GHSSignalWord =

| HPhrases = {{H-phrases|302|312|315|319|332|335}}

| PPhrases = {{P-phrases|261|280|305+351+338}}

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| Section4 = {{Chembox Related

| OtherCompounds = {{ubl|

• 3-Iodophenol
• 4-Iodophenol
• 2-Fluorophenol
• 2-Chlorophenol
• 2-Bromophenol

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}}

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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.{{cite web | url = https://www.sigmaaldrich.com/catalog/product/ALDRICH/281409 | publisher = Sigma-Aldrich | title= 2-Iodophenol}}

It can be prepared by treatment of 2-chloromercuriphenol with iodine:

:{{Chem2|ClHgC6H4OH + I2 -> IC6H4OH + HgCl(I)}}

Direct reaction of phenol with iodine gives a mixture of 2- and 4-iodo derivatives.{{cite journal |author1=Whitmore, F. C. |author2=Hanson, E. R.

|doi=10.15227/orgsyn.004.0037|title=o-Iodophenol|journal=Organic Syntheses |year=1925 |volume=4 |page=37 }}