108-43-0 3-Chlorophenol

LD50 oral dermal subcutaneous intraperitoneal LD50 inhalative 

Severe irritation of the rabbit skin (2mg/24h) and the rabbit eyes (0.25mg/24h). 

4-Chlorophenol which is easily synthesized by chlorination of phenol (7.1) in the cold exhibits considerable antibacterial and antifungal activity. However, these properties are practically of no avail in consideration of the high toxicity and the strong adhering odour of the substance. 

Microbicide group (substance class) Chemical name Chemical formula Structural formula 

Boiling point/range °C (101 kPa) Melting point °C Density g/ml (75°C) 

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A Methylamino)phenol. This derivative, also named 4-hydroxy-/V-methy1ani1ine (19), forms needles from benzene which are slightly soluble in ethanol andinsoluble in diethyl ether. Industrial synthesis involves decarboxylation of A/-(4-hydroxyphenyl)glycine [122-87-2] at elevated temperature in such solvents as chlorobenzene—cyclohexanone (184,185). It also can be prepared by the methylation of 4-aminophenol, or from methylamiae [74-89-5] by heating with 4-chlorophenol [106-48-9] and copper sulfate at 135°C in aqueous solution, or with hydroquinone [123-31 -9] 2l. 200—250°C in alcohoHc solution (186). 

Chlorophenol also enters into the synthesis of a biocide (57), 2-ben2yl-4-chlotophenol [120-32-1J. 

Another appHcation of 4-chlorophenol is in the synthesis of a dmg, ethyl a, a-dimethyl-4-chlorophenoxy acetate [637-07-0] (60), used as a cholesterol-reducing agent. This synthesis involves reaction with acetone and chloroform, followed by ethanol esterification. 

Another important bisphenol is dichlorophene (dichlorophane, methylene-bis(4-chlorophenol)) [97-23-4]. Whereas it is not as active against bacteria as hexachlorophane, it has found miscehaneous apphcations, eg, as a rot preservative for textiles (89) as a treatment for athlete s foot and for tapeworm in humans and domestic animals as a slimicide in paper manufacture and as an antibacterial agent in water-cooling systems (90). 

Dihydroxyanthraquinone. This anthraquinone, also known as quinizarin [81-64-1] (29), is of great importance in manufacturing disperse, acid, and vat dyes. It is manufactured by condensation of phthalic anhydride (27) with 4-chlorophenol [106-48-9] (28) in oleum in the presence of boric acid or boron trifluoride (40,41). Improved processes for reducing waste acid have been reported (42), and yield is around 80% on the basis of 4-chlorophenol. 

Nltroso-4-chlorophenol copper chelate (4) A solution of p-chlorophenol 3 (12 85 g,... 

Aminoanthraqumone, 12 Aminoazobenzene, 12 Aminoazotoluene, 12 2-Amino-4-chlorophenol, 12 2 - Amino-5 -diethylaminopentane, 12 Aminoethanol, 12... 

Notes. (1) Other phenols which undergo this type of reaction include 4-chlorophenol, m-cresol (3-methylphenol) and 2-naphthol. 

After drying for 10 min in a stream of cold air 1,4-phenylenediamine (h/Jj 5-10), 2-amino-4-chlorophenol (h/ f 15-20), 4-nitroaniline (h/ f 25-30) and l,4-amino-3-nitro-toluene (h/ f 50-55) appeared as blue-violet chromatogram zones on a blue background. These could be recognized without difficulty for several days from the back of the chromatogram. 

The detection limits per chromatogram zone lay between 5 ng (1,4-phenylenediamine, 4-nitroaniline) and 25 ng (2-amino-4-chlorophenol, 4-amino-3-nitrotoluene). 

Fig. 1 Reflectance scan of a chromatogram track with 125 ng each substance per chromatogram zone 1 = 1,4-phenylenediamine, 2 = 2-amino-4-chlorophenol, 3 = 4-nitroaniline, 4 = 4-amino-3-nitrotoluene.

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