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4-Chlorophenol

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4-Chlorophenol
Names
Preferred IUPAC name 4-Chlorophenol
Other names p-Chlorophenol
Identifiers
CAS Number
3D model (JSmol)
3DMet
Beilstein Reference 507004
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.003.094 Edit this at Wikidata
EC Number
  • 203-402-6
Gmelin Reference 2902
KEGG
PubChem CID
RTECS number
  • SK2800000
UNII
UN number 2020
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H5ClO/c7-5-1-3-6(8)4-2-5/h1-4,8HKey: WXNZTHHGJRFXKQ-UHFFFAOYSA-N
SMILES
  • C1=CC(=CC=C1O)Cl
Properties
Chemical formula C6H5ClO
Molar mass 128.56 g·mol
Appearance White solid
Density 1.2651 g/cm at 40 °C
Melting point 43.1 °C (109.6 °F; 316.2 K)
Boiling point 219 °C (426 °F; 492 K)
Solubility in water 27.1 g/L
Acidity (pKa) 9.41
Magnetic susceptibility (χ) -77.7·10 cm/mol
Refractive index (nD) 1.5579
Structure
Dipole moment 2.11 D
Thermochemistry
Std enthalpy of
formation (ΔfH298) 		-197.7 kJ·mol (s)
−181.3 kJ·mol (l)
Enthalpy of fusion (ΔfHfus) 14.1 kJ·mol
Hazards
GHS labelling:
Pictograms GHS05: CorrosiveGHS06: ToxicGHS07: Exclamation markGHS09: Environmental hazard
Signal word Danger
Hazard statements H290, H301, H302, H312, H314, H332, H411
Precautionary statements 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)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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.

It once was produced on a large scale as a precursor to hydroquinone. It is a classic precursor, upon reaction with phthalic anhydride, to quinizarin. The commercial dye quinizarin is produced by the reaction of phthalic anhydride and 4-chlorophenol followed by hydrolysis of the chloride.

Clofibrate, a drug for controlling the high cholesterol and triacylglyceride level in the blood, is derived from 4-chlorophenol.

References

  1. ^ 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. ^ 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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