4-Chlorophenol

4-Chlorophenol
Names
	Preferred IUPAC name 4-Chlorophenol
	Other names p-Chlorophenol
Identifiers
CAS Number	106-48-9;
3D model (JSmol)	Interactive image;
3DMet	B00391;
Beilstein Reference	507004
ChEBI	CHEBI:28078;
ChEMBL	ChEMBL57053;
ECHA InfoCard	100.003.094
EC Number	203-402-6;
Gmelin Reference	2902
KEGG	C02124;
PubChem CID	4684;
RTECS number	SK2800000;
UNII	3DLC36A01X;
UN number	2020
CompTox Dashboard (EPA)	DTXSID1021871 ;
	InChI InChI=1S/C6H5ClO/c7-5-1-3-6(8)4-2-5/h1-4,8H Key: WXNZTHHGJRFXKQ-UHFFFAOYSA-N;
	SMILES C1=CC(=CC=C1O)Cl;
Properties
Chemical formula	C6H5ClO
Molar mass	128.56 g·mol−1
Appearance	White solid
Density	1.2651 g/cm3 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)	-77.7·10−6 cm3/mol
Refractive index (nD)	1.5579
Structure
Dipole moment	2.11 D
Thermochemistry
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:
Pictograms
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 [77 °F], 100 kPa). Infobox references

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 pK_a 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

^ ^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

Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. ISBN 9781498754293.

[crc-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

[Ull2-7] 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.

[Ullmann-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.

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