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3-Iodophenol

3-Iodophenol
Names
IUPAC name
3-Iodophenol
Other names
    • m-Iodophenol
    • meta-Iodophenol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.009.931 Edit this at Wikidata
EC Number
  • 210-923-2
UNII
  • InChI=1S/C6H5IO/c7-5-2-1-3-6(8)4-5/h1-4,8H
    Key: FXTKWBZFNQHAAO-UHFFFAOYSA-N
  • C1=CC(=CC(=C1)I)O
Properties
C6H5IO
Molar mass 220.009 g·mol−1
Melting point 118 °C (244 °F; 391 K)[2]
Boiling point 186 °C (367 °F; 459 K)[2] (100 mmHg)
Acidity (pKa) 9.03[1]
Hazards
GHS labelling:[3]
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, 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).

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.[4] Well cited examples include thiolate[5] and amine nucleophiles.[6]

3-Iodophenol can be prepared by oxidative decarboxylation of 3-iodobenzoic acid:[7]

IC6H4CO2H + "O" → IC6H4OH + CO2

References

  1. ^ Haynes, p. 5.93
  2. ^ a b Haynes, p. 3.324
  3. ^ "3-Iodophenol". Sigma-Aldrich.
  4. ^ "3-Iodophenol". Fisher Scientific.
  5. ^ Kwong, Fuk Yee; Buchwald, Stephen L. (2002). "A General, Efficient, and Inexpensive Catalyst System for the Coupling of Aryl Iodides and Thiols". Organic Letters. 4 (20): 3517–3520. doi:10.1021/ol0266673. PMID 12323058.
  6. ^ Shen, Qilong; Ogata, Tokutaro; Hartwig, John F. (2008). "Highly Reactive, General and Long-Lived Catalysts for Palladium-Catalyzed Amination of Heteroaryl and Aryl Chlorides, Bromides, and Iodides: Scope and Structure–Activity Relationships". Journal of the American Chemical Society. 130 (20): 6586–6596. doi:10.1021/ja077074w. PMC 2822544. PMID 18444639.
  7. ^ Xiong, Wenzhang; Shi, Qiu; Liu, Wenbo H. (2022). "Simple and Practical Conversion of Benzoic Acids to Phenols at Room Temperature". Journal of the American Chemical Society. 144 (34): 15894–15902. doi:10.1021/jacs.2c07529. PMID 35997485. S2CID 251742827.

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