2,4,6-Tribromophenol

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.

2,4,6-Tribromophenol
Names
IUPAC name
2,4,6-Tribromophenol
Other names
Tribromophenol; 2,4,6-TBP; TBP
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.003.890
KEGG
UNII
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)[2]
286 °C[1]
Slightly soluble[1]
59-61 mg/L[3]
Hazards
GHS pictograms [4]
NFPA 704 (fire diamond)
Flammability code 0: Will not burn. E.g. waterHealth code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
0
2
0
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).
N verify (what is YN ?)
Infobox references

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.[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.[6][7]

Bismuth salt

The bismuth salt is the active ingredient in Xeroform 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]

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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. Concise International Chemical Assessment Document 66: 2,4,6-Tribromophenol and Other Simple Brominated Phenols, International Programme on Chemical Safety
  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. doi:10.1002/etc.5620200407. PMID 11345448.
  6. http://icl-ip.com/wp-content/uploads/2012/01/613WoodpreservativeICLIP.pdf
  7. https://core.ac.uk/download/pdf/39187475.pdf
  8. "MeSH Browser". meshb.nlm.nih.gov. Retrieved 2019-08-27.
  9. 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.
  10. 38,000 more bottles of Lipitor recalled over odor complaints, CNN.com, October 30, 2010
  11. Lipitor (atorvastatin) 40 mg: Recall Specific Bottles, drugs.com, Dec 23, 2010
  12. Tylenol Recall Expands, WebMD Health News, January 18, 2010
  13. 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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