3-Chlorophenol is an organic compound with the molecular formula C6H4ClOH. It is one of three isomers of monochlorophenol. It is a colorless or white solid that melts easily and exhibits significant solubility in water. Together with 3,5-dichlorophenol, it is prepared industrially by dechlorination of polychlorophenols. Alternatively, it arises via the cumene process, which starts with the alkylation of chlorobenzene with propylene.[6]
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| Names | |
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| Preferred IUPAC name
3-Chlorophenol[1] | |
| Other names
m-Chlorophenol
meta-Chlorophenol 3-Hydroxychlorobenzene | |
| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.003.257 |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C6H5ClO | |
| Molar mass | 128.56 g·mol−1 |
| Appearance | Colorless or white oily solid |
| Density | 1.245 g/cm3 at 45 °C[2] |
| Melting point | 32.5 °C (90.5 °F; 305.6 K)[2] |
| Boiling point | 210 °C (410 °F; 483 K)[2] |
| 20 g/L at 20 °C | |
| Solubility in other solvents | Soluble in ethanol, diethyl ether, benzene |
| Acidity (pKa) | 9.12[3] |
| -77.6·10−6 cm3/mol[4] | |
Refractive index (nD)
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1.5565[2] |
| Thermochemistry[5] | |
Std enthalpy of
formation (ΔfH⦵298) |
-206.4 kJ·mol−1 (s) −189.3 kJ·mol−1 (l) |
Enthalpy of fusion (ΔfH⦵fus)
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14.9 kJ·mol−1 |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards
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Corrosive – causes burns |
| Flash point | 120 °C (248 °F; 393 K) |
| 550 °C (1,022 °F; 823 K) | |
| Safety data sheet (SDS) | MSDS |
| Related compounds | |
Related aromatic
hydrocarbons |
Benzene Phenol Chlorobenzene |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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References
edit- ^ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 690. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
Only one name is retained, phenol, for C6H5-OH, both as a preferred name and for general nomenclature. The structure is substitutable at any position. Locants 2, 3, and 4 are recommended, not o, m, and p.
- ^ a b c d Haynes, p. 3.116
- ^ Haynes, p. 5.90
- ^ Haynes, p. 3.577
- ^ Haynes, pp. 5.10, 6.156
- ^ François Muller; Liliane Caillard (2011). "Chlorophenols". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a07_001.pub2. ISBN 978-3527306732.
Cited sources
edit- Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. ISBN 9781498754293.