4-Chlorophenol
4-Chlorophenol is an organic compound with the formula C6H4ClOH. It is one of three monochlorophenol isomers. It is a colorless or white solid that melts easily and exhibits significant solubility in water. Its pKa is 9.14.
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| Names | |
|---|---|
| Preferred IUPAC name
4-Chlorophenol | |
| Other names
p-Chlorophenol | |
| Identifiers | |
3D model (JSmol) |
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| 3DMet | |
| 507004 | |
| ChEBI | |
| ChEMBL | |
| ECHA InfoCard | 100.003.094 |
| EC Number |
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| 2902 | |
| KEGG | |
PubChem CID |
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| RTECS number |
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| UNII | |
| UN number | 2020 |
CompTox Dashboard (EPA) |
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| Properties | |
| C6H5ClO | |
| Molar mass | 128.56 g·mol−1 |
| Appearance | White solid |
| Density | 1.2651 g/cm3 at 40 °C[1] |
| Melting point | 43.1 °C (109.6 °F; 316.2 K)[1] |
| Boiling point | 219 °C (426 °F; 492 K)[1] |
| 27.1 g/L | |
| Acidity (pKa) | 9.41[2] |
| -77.7·10−6 cm3/mol[3] | |
Refractive index (nD) |
1.5579[1] |
| Structure[4] | |
| 2.11 D | |
| Thermochemistry[5] | |
Std enthalpy of formation (ΔfH⦵298) |
-197.7 kJ·mol−1 (s) −181.3 kJ·mol−1 (l) |
Enthalpy of fusion (ΔfH⦵fus) |
14.1 kJ·mol−1 |
| Hazards | |
| GHS labelling: | |
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| Danger | |
| H290, H301, H302, H312, H314, H332, H411 | |
| P234, P260, P261, P264, P270, P271, P273, P280, P301+P310, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P310, P312, P321, P322, P330, P363, P390, P391, P404, P405, P501 | |
| Flash point | 121 °C (250 °F; 394 K)[6] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references | |
Preparation and reaction
It is prepared by chlorination of phenol, preferably in polar solvents, which tends to yield the 4-chloro derivative. Direct chlorination of molten phenol favors the formation of 2-chlorophenol.[7]
It once was produced on a large scale as a precursor to hydroquinone.[7] It is a classic precursor, upon reaction with phthalic anhydride, to quinizarin.[8] The commercial dye quinizarin is produced by the reaction of phthalic anhydride and 4-chlorophenol followed by hydrolysis of the chloride.[9]
Clofibrate, a drug for controlling the high cholesterol and triacylglyceride level in the blood, is derived from 4-chlorophenol.
References
- Haynes, p. 3.116
- Haynes, p. 5.90
- Haynes, p. 3.577
- Haynes, p. 9.61
- Haynes, pp. 5.10, 6.156
- Haynes, p. 16.20
- Muller, François; Caillard, Liliane (2011). "Chlorophenols". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a07_001.pub2.
- Bigelow, L. A.; Reynolds, H. H. (1926). "Quinizarin". Org. Synth. 6: 78. doi:10.15227/orgsyn.006.0078.
- Bien, H.-S.; Stawitz, J.; Wunderlich, K. "Anthraquinone Dyes and Intermediates". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_355.
Cited sources
- Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. ISBN 9781498754293.
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