4-Chlorophenol

4-Chlorophenol
Names
Preferred IUPAC name
4-Chlorophenol
Other names
p-Chlorophenol
Identifiers
3D model (JSmol)
507004
ChEBI
ChEMBL
ChemSpider
DrugBank
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 (ΔfH⦵fus)
 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).

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

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

  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