2,4,6-Tribromophenol (TBP) is a

brominated In chemistry, halogenation is a chemical reaction which introduces one or more halogens into a chemical compound. Halide-containing compounds are pervasive, making this type of transformation important, e.g. in the production of polymers, drugs ...

derivative of

phenol Phenol (also known as carbolic acid, phenolic acid, or benzenol) is an aromatic organic compound with the molecular formula . It is a white crystalline solid that is volatile and can catch fire. The molecule consists of a phenyl group () ...

. It is used as a

fungicide Fungicides are pesticides used to kill parasitic fungi or their spores. Fungi can cause serious damage in agriculture, resulting in losses of yield and quality. Fungicides are used both in agriculture and to fight fungal infections in animals, ...

, as a wood preservative, and an intermediate in the preparation of

flame retardant Flame retardants are a diverse group of chemicals that are added to manufactured materials, such as plastics and textiles, and surface finishes and coatings. Flame retardants are activated by the presence of an combustion, ignition source and pr ...

Production

Although natural TBP has been identified in ocean sediments as a metabolite of marine fauna, the commercial product is prepared industrially. In 2001, the production volume of TBP was estimated to be 2500 tonnes/year in Japan and 9500 tonnes/year worldwide. TBP can be prepared by the controlled reaction of elemental bromine with phenol: :

Uses

The predominant use of TBP is as an intermediate in the preparation of flame retardants such as brominated

epoxy resin Epoxy is the family of basic components or cured end products of epoxy resins. Epoxy resins, also known as polyepoxides, are a class of reactive prepolymers and polymers which contain epoxide groups. The epoxide functional group is also co ...

s. TBP is reacted with

sodium hydroxide Sodium hydroxide, also known as lye and caustic soda, is an inorganic compound with the formula . It is a white solid ionic compound consisting of sodium cations and hydroxide anions . Sodium hydroxide is a highly corrosive base (chemistry), ...

to form the

sodium Sodium is a chemical element; it has Symbol (chemistry), symbol Na (from Neo-Latin ) and atomic number 11. It is a soft, silvery-white, highly reactive metal. Sodium is an alkali metal, being in group 1 element, group 1 of the peri ...

salt In common usage, salt is a mineral composed primarily of sodium chloride (NaCl). When used in food, especially in granulated form, it is more formally called table salt. In the form of a natural crystalline mineral, salt is also known as r ...

, which is used as a fungicide and wood preservative.

Bismuth salt

The

bismuth Bismuth is a chemical element; it has symbol Bi and atomic number 83. It is a post-transition metal and one of the pnictogens, with chemical properties resembling its lighter group 15 siblings arsenic and antimony. Elemental bismuth occurs nat ...

salt is the active ingredient in Xeroform dressing.

Metabolism

Microbial metabolism in products treated with TBP is known to produce

2,4,6-tribromoanisole 2,4,6-Tribromoanisole (TBA) is a chemical compound that is a bromine, brominated derivative of anisole. It is one of the chemicals responsible for cork taint. Tribromoanisole is a fungal metabolite of 2,4,6-Tribromophenol, 2,4,6-tribromophenol, ...

(TBA), which has a musty odor. In 2010 and 2011,

Pfizer Pfizer Inc. ( ) is an American Multinational corporation, multinational Pharmaceutical industry, pharmaceutical and biotechnology corporation headquartered at The Spiral (New York City), The Spiral in Manhattan, New York City. Founded in 184 ...

and

Johnson & Johnson Johnson & Johnson (J&J) is an American multinational pharmaceutical, biotechnology, and medical technologies corporation headquartered in New Brunswick, New Jersey, and publicly traded on the New York Stock Exchange. Its common stock is a c ...

voluntarily recalled some products due to TBA odors from wooden pallets which were treated with TBP.Tylenol Recall Expands
WebMD Health News, January 18, 2010
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References

{{DEFAULTSORT:Tribromophenol, 2, 4, 6- Fungicides Bromoarenes Phenols