2,4,6-Tribromophenol

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2,4,6-Tribromophenol
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Names
IUPAC name
2,4,6-Tribromophenol
Other names
Tribromophenol; 2,4,6-TBP; TBP
Identifiers
118-79-6 YesY
ChEBI CHEBI:47696 N
ChEMBL ChEMBL220087 YesY
ChemSpider 1438 YesY
DrugBank DB02417 YesY
Jmol 3D model Interactive image
KEGG C14454 YesY
PubChem 1483
  • InChI=1S/C6H3Br3O/c7-3-1-4(8)6(10)5(9)2-3/h1-2,10H YesY
    Key: BSWWXRFVMJHFBN-UHFFFAOYSA-N YesY
  • 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 330.80 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]
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
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.[2] TBP can be prepared by the controlled reaction of elemental bromine with phenol:[3]

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Uses

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

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

Metabolism

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

References

  1. ↑ 1.0 1.1 1.2 1.3 "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. ↑ 2.0 2.1 2.2 Concise International Chemical Assessment Document 66: 2,4,6-Tribromophenol and Other Simple Brominated Phenols, International Programme on Chemical Safety
  3. ↑ 3.0 3.1 Merck Index, 11th Edition, 9526
  4. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ http://www.nlm.nih.gov/cgi/mesh/2008/MB_cgi?field=uid&term=C004554
  6. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  7. ↑ 38,000 more bottles of Lipitor recalled over odor complaints, CNN.com, October 30, 2010
  8. ↑ Lipitor (atorvastatin) 40 mg: Recall Specific Bottles, drugs.com, Dec 23, 2010
  9. ↑ Tylenol Recall Expands, WebMD Health News, January 18, 2010
  10. ↑ 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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