2,4,6-Tribromophenol

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2,4,6-Tribromophenol
2,4,6-Tribromophenol.png
2,4,6-Tribromophenol-3D-balls.png
Names
IUPAC name
2,4,6-Tribromophenol
Other names
Tribromophenol; 2,4,6-TBP; TBP
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
DrugBank
ECHA InfoCard 100.003.890
KEGG
Properties
C6H3Br3O
Molar mass 330.80 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 GHS-pictogram-exclam.svgGHS-pictogram-pollu.svg[4]
NFPA 704
Flammability code 0: Will not burn. E.g., water Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Lethal dose or concentration (LD, LC):
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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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[edit]

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]

2,4,6-tribromophenol synthesis.PNG

Uses[edit]

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.

Bismuth salt[edit]

The bismuth salt is the active ingredient in Xeroform dressing.[6]

Metabolism[edit]

Microbial metabolism in products treated with TBP is known to produce 2,4,6-tribromoanisole (TBA),[7] 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.[8][9][10][11]

References[edit]

  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 978-0-471-73518-2, page 632
  2. ^ a b c Concise International Chemical Assessment Document 66: 2,4,6-Tribromophenol and Other Simple Brominated Phenols, International Programme on Chemical Safety
  3. ^ a b Merck Index, 11th Edition, 9526
  4. ^ Sigma-Aldrich Co., 2,4,6-Tribromophenol. Retrieved on 2015-02-19.
  5. ^ 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. PMID 11345448. doi:10.1002/etc.5620200407. 
  6. ^ http://www.nlm.nih.gov/cgi/mesh/2008/MB_cgi?field=uid&term=C004554
  7. ^ 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. 
  8. ^ 38,000 more bottles of Lipitor recalled over odor complaints, CNN.com, October 30, 2010
  9. ^ Lipitor (atorvastatin) 40 mg: Recall Specific Bottles, drugs.com, Dec 23, 2010
  10. ^ Tylenol Recall Expands, WebMD Health News, January 18, 2010
  11. ^ McNeil Consumer Healthcare Announces Voluntary Recall Of One Product Lot Of TYLENOL® Extra Strength Caplets 225 Count Distributed In The U.S.