Chloro-3,5-Xylenol

Therapeutic Function Topical antiseptic and disinfectant Chemical Name 4-Chloro-3,5-dimethylphenol Common Name — 

Trade Name Manufacturer Country Year Introduced 

The following method is described in U.S. Patent 2,430,891. To a solution of 10 parts of tris-p-methoxyphenyl ethylene in 35 to 40 parts of carbon tetrachloride Is added a solution of 2.0 parts of chlorine in 50 parts of carbon tetrachloride, with stirring, and over a period of Vj hour. The carbon tetrachloride is then removed by distillation on a steam bath and the residual oil is recrystallized from 250 to 400 parts of methanol, decolorizing with charcoal or the like if necessary. Tris-p-methoxyphenyl chloroethylene is obtained in a yield of 65 to 75%. It melts at 113° to 114°C. 

2-chlor-m-5-xylenol can be obtained having a melting point of 11210 to 115°C. The material can be purified if desired by crystallization from a solvent such as a hydrocarbon. 

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Synonyms 4-chloro-3-xylenol 2-chloro-m-xylenol 2-chloro-5-hydroxy-m-xylene 2-chloro-5-hydroxy-i,3-dimethylbenzene 4-chloro-... 

SYNS BENZYTOL 4-CHLORO-3.5-DIMETHYL-PHENOL CHLORO-XYLENOL p-CHLORO-m-XYLENOL DESSON DETTOL ESPADOL HUSEPT EXTRA OTTASEPT OTTASEPT EXTRA PCMX RBA 777... 

Cm.OROCARBONSANDCm.OROHYDROCARBONS - BENZYL CTD ORIDE, BENZAL CTD ORIDE AND BENZOTRICm ORIDE] (Vol 6) p-Chloro-m-xylenol [88-04-0]... 

X5lenol is an important starting material for insecticides, xylenol—formaldehyde resins, disinfectants, wood preservatives, and for synthesis of a-tocopherol (vitamin E) (258) and i7/-a-tocopherol acetate (USP 34-50/kg, October 1994). The Bayer insecticide Methiocarb is manufactured by reaction of 3,5-x5lenol with methylsulfenyl chloride to yield 4-methylmercapto-3,5-xylenol, followed by reaction with methyl isocyanate (257). Disinfectants and preservatives are produced by chlorination to 4-chloro- and 2,4-dich1oro-3,5-dimethylpheno1 (251). 

Sodium a-sulfomethylmyristate is the major component of a clear, antiseptic, liquid cleanser especially for use on the skin. A disinfectant such as fluoro-phene, bithionol, p-chloro-m-xylenol, or hexachlorophene is added, and also a high-quality animal, vegetable, mineral, or synthetic oil and an alkyl ether of polyethylene glycol [87]. 

Many derivatives of phenol are now made by a synthetic process. Homologous series of substituted derivatives have been prepared and tested for antimicrobial activity. A combination of alkyl substitution and halogenation has produced useful derivatives including clorinated phenols which are constituents of a number of proprietary disinfectants. Two ofthe most widely used derivatives are/ -chloro-m-cresol (4-chloro-3-methylphenol, chlorocresol, Fig. 10.7C) which is mostly employed as a preservative at a concentration of 0.1%, and / -chloro-m-xylenol (4-chloro-3,5-dimethylphenol, chloroxylenol. Fig. 10.7C) which is used for skin disinfection, although less than formerly. Chloroxylenol is sparingly soluble in water and must be solubihzed, for example in a suitable soap solution in conjunction with terpineol or pine oil. Its antimicrobial capacity is weak and is reduced by the presence of organic matter. 

Sodium orthophenyl phenate remains an important ingredient in the treatment of cooling waters. Both orthophenyl and its sodium salt have a wide spectmm of preservative use, including caulks, construction products, and leather processing. Similady, zra-chloro-z /tf-xylenol is used to preserve a number of water-based goods, including inks (qv), emulsions, and shoe polish, in addition to providing mold resistance to leather. 

Chloro-m-cresol p-Chloro-TO-xylenol 6-Amino-m-cresol68... 

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