2,4,6-Tribromophenol

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:

: [[File:2,4,6-Tribromphenol Reaktionsschemata.svg|300px]]

Uses

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

Bismuth salt

The bismuth salt is the active ingredient in Xeroform dressing.

Metabolism

Microbial metabolism in products treated with TBP is known to produce 2,4,6-tribromoanisole (TBA), which has a musty odor. In 2010 and 2011, Pfizer and Johnson & Johnson voluntarily recalled some products due to TBA odors from wooden pallets which were treated with TBP.

References

References

1. "'''3851''': Tribromophenol" in ''Gardner's Commercially Important Chemicals: Synonyms, Trade Names, and Properties'', G. W. A. Milne (Editor), {{ISBN. 978-0-471-73518-2, page 632
2. ''[[Merck Index]]'', 11th Edition, '''9526'''
3. 
   59-61 mg/L[http://www.inchem.org/documents/cicads/cicads/cicad66.htm#4.2 Concise International Chemical Assessment Document 66: 2,4,6-Tribromophenol and Other Simple Brominated Phenols], International Programme on Chemical Safety
4. {{Sigma-Aldrich. Fluka
5. (2001). "Polychaete indicator species as a source of natural halogenated organic compounds in marine sediments". Environmental Toxicology and Chemistry.
6. "2,4,6 Tribromophenol".
7. (1989). "Laboratory Evaluation of Chemicals as Wood {{not a typo". Kyoto University.
8. "MeSH Browser".
9. (1997). "2,4,6-Tribromoanisole: a Potential Cause of Mustiness in Packaged Food". J. Agric. Food Chem..
10. [http://www.cnn.com/2010/HEALTH/10/30/lipitor.recall/ 38,000 more bottles of Lipitor recalled over odor complaints], CNN.com, October 30, 2010
11. [https://www.drugs.com/fda/lipitor-atorvastatin-40-mg-recall-specific-bottles-12873.html Lipitor (atorvastatin) 40 mg: Recall Specific Bottles], drugs.com, Dec 23, 2010
12. [http://arthritis.webmd.com/news/20091229/tylenol-recall-expands Tylenol Recall Expands], WebMD Health News, January 18, 2010
13. [https://web.archive.org/web/20110702052750/http://www.fda.gov/Safety/Recalls/ucm261498.htm McNeil Consumer Healthcare Announces Voluntary Recall Of One Product Lot Of TYLENOL Extra Strength Caplets 225 Count Distributed In The U.S.]