3-Iodophenol

3-Iodophenol
Names
	IUPAC name 3-Iodophenol
	Other names m-Iodophenol; meta-Iodophenol; ;
Identifiers
CAS Number	626-02-8 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:33439;
ChEMBL	ChEMBL115335;
ChemSpider	11769;
ECHA InfoCard	100.009.931
EC Number	210-923-2;
PubChem CID	12272;
UNII	YU584Z4CZN;
CompTox Dashboard (EPA)	DTXSID3052305 ;
	InChI InChI=1S/C6H5IO/c7-5-2-1-3-6(8)4-5/h1-4,8H Key: FXTKWBZFNQHAAO-UHFFFAOYSA-N;
	SMILES C1=CC(=CC(=C1)I)O;
Properties
Chemical formula	C6H5IO
Molar mass	220.009 g·mol−1
Melting point	118 °C (244 °F; 391 K)
Boiling point	186 °C (367 °F; 459 K) (100 mmHg)
Acidity (pKa)	9.03
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P305 P351 P338
Related compounds
Related compounds	2-Iodophenol; 4-Iodophenol; 3-Fluorophenol; 3-Chlorophenol; 3-Bromophenol; ;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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

^ 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

Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. ISBN 9781498754293.

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[1] Haynes, p. 5.93

[crc-2] Haynes, p. 3.324

[SigmaAldrich-3] "3-Iodophenol". Sigma-Aldrich.

[Fisher-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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