3-Iodophenol

{{Chembox

|ImageFile = 3-Iodophenol.svg

|ImageSize = 120px

|IUPACName = 3-Iodophenol

|OtherNames = {{ubl|

• m-Iodophenol
• meta-Iodophenol

}}

| Section1 = {{Chembox Identifiers

| CASNo = 626-02-8

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

| ChEBI = 33439

| ChEMBL = 115335

| EC_number = 210-923-2

| PubChem = 12272

| ChemSpiderID = 11769

| UNII = YU584Z4CZN

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

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

| InChIKey = FXTKWBZFNQHAAO-UHFFFAOYSA-N

}}

| Section2 = {{Chembox Properties

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

| Density =

| MeltingPtC = 118

| MeltingPt_ref = Haynes, p. 3.324

| BoilingPtC = 186

| BoilingPt_notes= (100 mmHg)

| BoilingPt_ref =

| pKa = 9.03Haynes, p. 5.93

}}

| Section3 = {{Chembox Hazards

| MainHazards =

| NFPA-H =

| NFPA-F =

| NFPA-I =

| NFPA-S =

| GHS_ref={{cite web | url = https://www.sigmaaldrich.com/catalog/product/ALDRICH/I10007 | publisher = Sigma-Aldrich | title= 3-Iodophenol}}

| GHSPictograms = {{GHS exclamation mark}}

| GHSSignalWord = warning

| HPhrases = {{H-phrases|315|319|335}}

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

}}

| Section4 = {{Chembox Related

| OtherCompounds = {{ubl|

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

}}

}}

}}

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.{{cite web | url = https://www.fishersci.com/shop/products/3-iodophenol-98-thermo-scientific/AAA1115509 | publisher = Fisher Scientific | title= 3-Iodophenol}} Well cited examples include thiolate{{cite journal |doi=10.1021/ol0266673|title=A General, Efficient, and Inexpensive Catalyst System for the Coupling of Aryl Iodides and Thiols |year=2002 |last1=Kwong |first1=Fuk Yee |last2=Buchwald |first2=Stephen L. |journal=Organic Letters |volume=4 |issue=20 |pages=3517–3520 |pmid=12323058 }} and amine nucleophiles.{{cite journal |doi=10.1021/ja077074w|title=Highly Reactive, General and Long-Lived Catalysts for Palladium-Catalyzed Amination of Heteroaryl and Aryl Chlorides, Bromides, and Iodides: Scope and Structure–Activity Relationships |year=2008 |last1=Shen |first1=Qilong |last2=Ogata |first2=Tokutaro |last3=Hartwig |first3=John F. |journal=Journal of the American Chemical Society |volume=130 |issue=20 |pages=6586–6596 |pmid=18444639 |pmc=2822544 }}

3-Iodophenol can be prepared by oxidative decarboxylation of 3-iodobenzoic acid:{{cite journal |doi=10.1021/jacs.2c07529|title=Simple and Practical Conversion of Benzoic Acids to Phenols at Room Temperature |year=2022 |last1=Xiong |first1=Wenzhang |last2=Shi |first2=Qiu |last3=Liu |first3=Wenbo H. |journal=Journal of the American Chemical Society |volume=144 |issue=34 |pages=15894–15902 |pmid=35997485 |s2cid=251742827 }}

:{{chem2|IC6H4CO2H + "O" -> IC6H4OH + CO2}}