2-Iodophenol
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.[1]
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| Names | |
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| IUPAC name
2-Iodophenol | |
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 | 1.947 g/cm3 |
| Melting point | 37–40 °C (99–104 °F; 310–313 K)[1] |
| Boiling point | 186–187 °C (367–369 °F; 459–460 K)[1] (160 mmHg) |
| Acidity (pKa) | 8.46[2] |
| Hazards | |
| GHS labelling: | |
 [1] | |
| 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).
Infobox references | |
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.[3]
References
- "2-Iodophenol". Sigma-Aldrich.
- Rappoport (1984). CRC Handbook of Tables for Organic Compound Identification (3rd ed.). ISBN 0-8493-0303-6.
- F. C. Whitmore, E. R. Hanson (1925). "o-Iodophenol". Organic Syntheses. 4: 37. doi:10.15227/orgsyn.004.0037.
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