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]
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| Names | |
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| IUPAC name
2-Iodophenol
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Other names
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| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.007.792 |
| EC Number |
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| 406034 | |
| KEGG | |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C6H5IO | |
| Molar mass | 220.009 g·mol−1 |
| Density | 1.8757 g/cm3 (80 °C)[1] |
| Melting point | 43 °C (109 °F; 316 K)[1] |
| Boiling point | 186 °C (367 °F; 459 K)[1] (160 mmHg) |
| Acidity (pKa) | 8.51[2] |
| Hazards | |
| GHS labelling: | |
 [3]
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| H302, H312, H315, H319, H332, H335 | |
| P261, P280, 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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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
edit- ^ 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
edit- Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. ISBN 9781498754293.
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