3-Iodophenol
Appearance
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Names | |
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IUPAC name
3-Iodophenol
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Other names
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Identifiers | |
3D model (JSmol)
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ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.009.931 |
EC Number |
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PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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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] | |
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Warning | |
H315, H319, H335 | |
P261, P305+P351+P338 | |
Related compounds | |
Related compounds
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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
[edit]- ^ Haynes, p. 5.93
- ^ a b Haynes, p. 3.324
- ^ "3-Iodophenol". Sigma-Aldrich.
- ^ "3-Iodophenol". Fisher Scientific.
- ^ 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.
- ^ 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.
- ^ 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.
Cited sources
[edit]- Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. ISBN 9781498754293.