2-Iodophenol

2-Iodophenol
Names
	IUPAC name 2-Iodophenol
	Other names o-Iodophenol; ortho-Iodophenol; ;
Identifiers
CAS Number	533-58-4 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:16706;
ChEMBL	ChEMBL225564;
ChemSpider	10328;
ECHA InfoCard	100.007.792
EC Number	208-569-9;
Gmelin Reference	406034
KEGG	C01874;
PubChem CID	10784;
UNII	F27L34A8B9;
CompTox Dashboard (EPA)	DTXSID5052175 ;
	InChI InChI=1S/C6H5IO/c7-5-3-1-2-4-6(5)8/h1-4,8H Key: KQDJTBPASNJQFQ-UHFFFAOYSA-N;
	SMILES C1=CC=C(C(=C1)O)I;
Properties
Chemical formula	C6H5IO
Molar mass	220.009 g·mol−1
Density	1.8757 g/cm3 (80 °C)
Melting point	43 °C (109 °F; 316 K)
Boiling point	186 °C (367 °F; 459 K) (160 mmHg)
Acidity (pKa)	8.51
Hazards
	GHS labelling:
Pictograms
Hazard statements	H302, H312, H315, H319, H332, H335
Precautionary statements	P261, P280, P305+P351+P338
Related compounds
Related compounds	3-Iodophenol; 4-Iodophenol; 2-Fluorophenol; 2-Chlorophenol; 2-Bromophenol; ;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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.^[3]

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

ClHgC₆H₄OH + I₂ → IC₆H₄OH + HgCl(I)

Direct reaction of phenol with iodine gives a mixture of 2- and 4-iodo derivatives.^[4]

References

^ ^a ^b ^c Haynes, p. 3.324
^ Haynes, p. 5.93
^ ^a ^b "2-Iodophenol". Sigma-Aldrich.
^ Whitmore, F. C.; Hanson, E. R. (1925). "o-Iodophenol". Organic Syntheses. 4: 37. doi:10.15227/orgsyn.004.0037.

Cited sources

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

[crc-1] Haynes, p. 3.324

[2] Haynes, p. 5.93

[SigmaAldrich-3] "2-Iodophenol". Sigma-Aldrich.

[4] Whitmore, F. C.; Hanson, E. R. (1925). "o-Iodophenol". Organic Syntheses. 4: 37. doi:10.15227/orgsyn.004.0037.

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