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
Preferred 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 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C6H3Br3O/c7-3-1-4(8)6(10)5(9)2-3/h1-2,10H Yes check.svgY
    Key: BSWWXRFVMJHFBN-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C6H3Br3O/c7-3-1-4(8)6(10)5(9)2-3/h1-2,10H
    Key: BSWWXRFVMJHFBN-UHFFFAOYAF
  • Brc1cc(Br)cc(Br)c1O
Properties
C6H3Br3O
Molar mass 330.801 g·mol−1
AppearanceWhite 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 labelling:
GHS-pictogram-exclam.svg GHS-pictogram-pollu.svg [4]
NFPA 704 (fire diamond)
NFPA 704.svgHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
0
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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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. [3] TBP can be prepared by the controlled reaction of elemental bromine with phenol: [2]

2,4,6-Tribromphenol Reaktionsschemata.svg

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[ 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. 1 2 3 4 5 "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. 1 2 Merck Index , 11th Edition, 9526
  3. 1 2 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. S2CID   42911887.
  6. ↑ "2,4,6 Tribromophenol" (PDF). ICL Industrial Products. Archived from the original (PDF) on August 27, 2019. Retrieved April 13, 2022.
  7. ↑ Tsunoda K, Takahashi M (1989). "Laboratory Evaluation of Chemicals as Wood Prerservatives: (1) Tribromophenol" (PDF). Wood Research. 76. Kyoto University: 39–48.
  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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