4-Chlorophenol

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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.

4-Chlorophenol
Names
Preferred IUPAC name
4-Chlorophenol
Other names
p-Chlorophenol
Identifiers
3D model (JSmol)
3DMet
507004
ChEBI
ChEMBL
ECHA InfoCard 100.003.094 Edit this at Wikidata
EC Number
  • 203-402-6
2902
KEGG
RTECS number
  • SK2800000
UNII
UN number 2020
  • InChI=1S/C6H5ClO/c7-5-1-3-6(8)4-2-5/h1-4,8H
    Key: WXNZTHHGJRFXKQ-UHFFFAOYSA-N
  • C1=CC(=CC=C1O)Cl
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]
1.5579[1]
Structure[4]
2.11 D
Thermochemistry[5]
-197.7 kJ·mol−1 (s)
−181.3 kJ·mol−1 (l)
Enthalpy of fusion fHfus)
14.1 kJ·mol−1
Hazards
GHS labelling:
GHS05: CorrosiveGHS06: ToxicGHS07: Exclamation markGHS09: Environmental hazard
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).

Preparation and reaction

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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

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  1. ^ a b c d Haynes, p. 3.116
  2. ^ Haynes, p. 5.90
  3. ^ Haynes, p. 3.577
  4. ^ Haynes, p. 9.61
  5. ^ Haynes, pp. 5.10, 6.156
  6. ^ Haynes, p. 16.20
  7. ^ 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.
  8. ^ Bigelow, L. A.; Reynolds, H. H. (1926). "Quinizarin". Org. Synth. 6: 78. doi:10.15227/orgsyn.006.0078.
  9. ^ 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

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