4-Chlorophenol

4-Chlorophenol
Names
	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	1.31 g/cm3
Melting point	42.8 °C (109.0 °F; 315.9 K)
Boiling point	217 °C (423 °F; 490 K)
Solubility in water	27.1 g/L
Refractive index (nD)	1.5579
Hazards
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H290, H301, H302, H312, H314, H318, H332, H411
GHS precautionary statements	P234, P260, P261, P264, P270, P271, P273, P280, P301+310, P301+312, P301+330+331, P302+352, P303+361+353, P304+312, P304+340, P305+351+338, P310, P312, P321, P322, P330, P363, P390, P391, P404
	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 ClC₆H₄OH. 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.[1]

It once was produced on a large scale as a precursor to hydroquinone.[1] It is a classic precursor, upon reaction with phthalic anhydride, to quinizarin.[2] The commercial dye quinizarin is produced by the reaction of phthalic anhydride and 4-chlorophenol followed by hydrolysis of the chloride.[3]

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

References

François Muller; Liliane Caillard (2011). "Chlorophenols". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a07_001.pub2.
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.

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[Ull2-1] François Muller; Liliane Caillard (2011). "Chlorophenols". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a07_001.pub2.

[2] Bigelow, L. A.; Reynolds, H. H. (1926). "Quinizarin". Org. Synth. 6: 78. doi:10.15227/orgsyn.006.0078.

[Ullmann-3] 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.