4-Chlorophenol
Appearance
Names | |
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Preferred IUPAC name
4-Chlorophenol | |
Other names
p-Chlorophenol
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Identifiers | |
3D model (JSmol)
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507004 | |
ChEBI | |
ChEMBL | |
ChemSpider | |
DrugBank | |
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)
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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)
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14.1 kJ·mol−1 |
Hazards | |
GHS labelling: | |
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).
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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.
Preparation and reaction
[edit]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]
References
[edit]- ^ a b c d 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
- ^ a b Muller, François; Caillard, Liliane (2011). "Chlorophenols". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a07_001.pub2. ISBN 978-3527306732.
- ^ 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. ISBN 978-3527306732.
Cited sources
[edit]- Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. ISBN 9781498754293.