2,4,6-Tribromophenol

2,4,6-Tribromophenol
IUPAC name

2,4,6-Tribromophenol
Other names

Tribromophenol; 2,4,6-TBP; TBP
Identifiers
CAS number 118-79-6 Y
PubChem 1483
ChemSpider 1438 Y
DrugBank DB02417
KEGG C14454 Y
ChEMBL CHEMBL220087 Y
Jmol-3D images Image 1
Properties
Molecular formula C6H3Br3O
Molar mass 330.8 g mol−1
Appearance White needles or prisms[1]
Melting point

95.5 °C[1]
Boiling point

244 °C[2]
286 °C[1]
Solubility in water Slightly soluble[1]
59-61 mg/L[3]
Hazards
LD50 2000 mg/kg (rat, oral)[1]
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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,[4] 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.[3] TBP can be prepared by the controlled reaction of elemental bromine with phenol:[2]

Uses

The predominant use of TBP is as an intermediate in the preparation of flame retardants such as brominated epoxy resins.[3] TBP is reacted with sodium hydroxide to form the sodium salt, which is used as a fungicide and wood preservative.

The bismuth salt is the active ingredient in Xeroform dressing.[5]

Microbial metabolism in products treated with TBP is known to produce 2,4,6-tribromoanisole.[6]

References

  1. ^ a b c d e "3851: Tribromophenol" in Gardner's Commercially Important Chemicals: Synonyms, Trade Names, and Properties, G. W. A. Milne (Editor), ISBN 978-0471735182, page 632
  2. ^ a b Merck Index, 11th Edition, 9526
  3. ^ a b c Concise International Chemical Assessment Document 66: 2,4,6-Tribromophenol and Other Simple Brominated Phenols, International Programme on Chemical Safety
  4. ^ Fielman KT, Woodin SA, Lincoln DE (2001). "Polychaete indicator species as a source of natural halogenated organic compounds in marine sediments". Environmental Toxicology and Chemistry 20 (4): 738–747. doi:10.1002/etc.5620200407. PMID 11345448. 
  5. ^ http://www.nlm.nih.gov/cgi/mesh/2008/MB_cgi?field=uid&term=C004554
  6. ^ Frank B. Whitfield, Jodie L. Hill, and 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.