Chemistry:2,4,6-Tribromophenol
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| Names | |||
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| Preferred IUPAC name
2,4,6-Tribromophenol | |||
| Other names
Tribromophenol; 2,4,6-TBP; TBP
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| Properties | |||
| C6H3Br3O | |||
| Molar mass | 330.801 g·mol−1 | ||
| Appearance | White needles or prisms[1] | ||
| Melting point | 95.5 °C (203.9 °F; 368.6 K)[1] | ||
| Boiling point | 244 °C (471 °F; 517 K)[3] 286 °C[1] | ||
| Slightly soluble[1] 59-61 mg/L[2] | |||
| Hazards | |||
| GHS pictograms |   [4]
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| NFPA 704 (fire diamond) | |||
| Lethal dose or concentration (LD, LC): | |||
LD50 (median dose)
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2000 mg/kg (rat, oral)[1] | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |||
 verify (what is   ?)
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| Infobox references | |||
2,4,6-Tribromophenol (TBP) is a brominated derivative of phenol. It is used as a fungicide, as a wood preservative, and an intermediate in the preparation of flame retardants.
Production
Although natural TBP has been identified in ocean sediments as a metabolite of marine fauna,[5] 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.[2] TBP can be prepared by the controlled reaction of elemental bromine with phenol:[3]
Uses
The predominant use of TBP is as an intermediate in the preparation of flame retardants such as brominated epoxy resins.[2] TBP is reacted with sodium hydroxide to form the sodium salt, which is used as a fungicide and wood preservative.[6][7]
Bismuth salt
The bismuth salt is the active ingredient in Xeroform[clarification needed] dressing.[8]
Metabolism
Microbial metabolism in products treated with TBP is known to produce 2,4,6-tribromoanisole (TBA),[9] 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.[10][11][12][13]
References
- ↑ 1.0 1.1 1.2 1.3 1.4 "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
- ↑ 2.0 2.1 2.2 Concise International Chemical Assessment Document 66: 2,4,6-Tribromophenol and Other Simple Brominated Phenols, International Programme on Chemical Safety
- ↑ 3.0 3.1 Merck Index, 11th Edition, 9526
- ↑ Sigma-Aldrich Co., 2,4,6-Tribromophenol. Retrieved on 2015-02-19.
- ↑ "Polychaete indicator species as a source of natural halogenated organic compounds in marine sediments". Environmental Toxicology and Chemistry 20 (4): 738–747. 2001. doi:10.1002/etc.5620200407. PMID 11345448.
- ↑ "2,4,6 Tribromophenol". https://www.icl-ip.com/wp-content/uploads/2012/01/613WoodpreservativeICLIP.pdf.
- ↑ Tsunoda, Kunio; Takahashi, Munezoh (1989). "Laboratory Evaluation of Chemicals as Wood Prerservatives: (1) Tribromophenol". Wood Research (Kyoto University) 76: 39–48. https://core.ac.uk/download/pdf/39187475.pdf.
- ↑ "MeSH Browser". https://meshb.nlm.nih.gov/#/record/ui?ui=C004554.
- ↑ Frank B. Whitfield; Jodie L. Hill; Kevin J. Shaw (1997). "2,4,6-Tribromoanisole: a Potential Cause of Mustiness in Packaged Food". J. Agric. Food Chem. 45 (3): 889–893. doi:10.1021/jf960587u.
- ↑ 38,000 more bottles of Lipitor recalled over odor complaints, CNN.com, October 30, 2010
- ↑ Lipitor (atorvastatin) 40 mg: Recall Specific Bottles, drugs.com, Dec 23, 2010
- ↑ Tylenol Recall Expands, WebMD Health News, January 18, 2010
- ↑ McNeil Consumer Healthcare Announces Voluntary Recall Of One Product Lot Of TYLENOL Extra Strength Caplets 225 Count Distributed In The U.S.
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