Hexachlorophene
chemical compound
Hexachlorophene, also known as Nabac, is an organochlorine compound that was once widely used as a disinfectant. The compound occurs as a white odorless solid, although commercial samples can be off-white and possess a slightly phenolic odor. It is insoluble in water but dissolves in acetone, ethanol, diethyl ether, and chloroform. In medicine, hexachlorophene is useful as a topical anti-infective and anti-bacterial agent. It is also used in agriculture as a soil fungicide, plant bactericide, and acaricide. It has also been reported to bind tubulin, blocking its polymerization.
Production
Hexachlorophene is produced by alkylation of 2,4,5-trichlorophenol with formaldehyde. Related antiseptics are prepared similarly, e.g., bromochlorophene and dichlorophene.
Safety
The LD50 (oral, rat) is 59 mg/kg, indicating that the compound is relatively toxic. It is neither mutagenic nor teratogenic according to Ullmann's Encyclopedia, but "embryotoxic and produces some teratogenic effects" according to the International Agency for Research on Cancer.
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