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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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Identifiers | |||
3D model (
JSmol)
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ChEBI | |||
ChEMBL | |||
ChemSpider | |||
DrugBank | |||
ECHA InfoCard | 100.003.890 | ||
KEGG | |||
PubChem
CID
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UNII | |||
CompTox Dashboard (
EPA)
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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 labelling: | |||
[4] | |||
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).
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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.
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]
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]
The bismuth salt is the active ingredient in Xeroform[ clarification needed] dressing. [8]
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]