Chloro-2-hydroxybiphenyl

MCOPP is much more effective than Chlorophen (7.3.5.) and was used in pine oil/soap based disinfectants as an active ingredient. However, the unfavourable toxicological properties of MCOPP have led to this application being discontinued. 

On account of their lessening importance only the main representatives of polychlorinated phenols will be the subject of the following brief description. 

Microbicide group (substance class) Chemical name Chemieal formula Struetural formula 

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Birds and mammals exposed to PCB mixtures frequently react differently. PCBs generally elicit large-colloid goiters in birds these goiters are inherently different from hyperplastic goiters produced in mammals exposed to PCBs. Fish-eating seabirds, such as the razorbill (Alca torda), can rapidly metabolize PCB congeners that have at least one pair of adjacent unsubstituted metapara combinations in the biphenyl moiety. Razorbills metabolized 4-chlorobiphenyl to 4-chloro-4 hydroxybiphenyl however. 

Sondossi, M., Sylvestre, M., Ahmad, D. Masse, R. (1991). Metabolismof hydroxybiphenyl and chloro-hydroxybiphenyl by biphenyl/chlorobiphenyl degrad i ng Pseudomonas testosteroni, strain B-356- Journal of Industrial Microbiology, 7, 77-88. 

The MultiCASE system has been used to identify a common 6-A unit biophore on a range of hormonally active chemicals with estrogenic activity that act as endocrine disruptors. This structural feature is a spacer biophore that is thought to be involved in the molecules binding to the estrogen receptor and is found on the standard estrogenic chemical, 17-beta-estradiol (see Combes, 2000). Other examples of molecules possessing this biophore include 4-hydroxytamoxifen, 2-chloro-4-hydroxybiphenyl, 3,4-dihydroxyfluorene, and 2,2-(fcE-4-hydroxyphenyl-1,1,1 -trichloroethane). 

Alkali hypochlorite solutions can be employed in chlorinating hydroxy- or methoxybiphenyl. One mole of 4-hydroxybiphenyl is dissolved in 1 mole of caustic soda and 6 liters of water. The solution is cooled, and 1 mole of sodium hypochlorite in solution is added slowly, with constant stirring. The reaction mixture is allowed to stand for about 1 hr and then warmed to 40 C. After filtration and cooling, 3-chloro-4-hydroxybiphenyl is precipitated by the addition of hydrochloric acid. 

Chloro-, bromo- and fluorobenzenes were hydrolyzed to phenol upon photolysis in water at different pHs chlorobenzene reacted markedly faster than the other halo derivatives [228]. Photosubstitution likewise occurred to some extent with various mcta-substitutedhalobenzenes [229]. Interesting was the case of monochlorobiphenyls in water in all cases variable amounts of hydroxybiphenyls were formed, but through a different mechanism according to the position of the chlorine on the aromatic ring [230,231]. 

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