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]

gollark: And mark that method as unsafe since *in its current form it is not safe*.
gollark: You should get someone to code-review it, though.
gollark: ```Instead of the programs I had hoped for, there came only a shuddering blackness and ineffable loneliness; and I saw at last a fearful truth which no one had ever dared to breathe before — the unwhisperable secret of secrets — The fact that this language of stone and stridor is not a sentient perpetuation of Rust as London is of Old London and Paris of Old Paris, but that it is in fact quite unsafe, its sprawling body imperfectly embalmed and infested with queer animate things which have nothing to do with it as it was in compilation.```
gollark: https://doc.rust-lang.org/nomicon/index.html
gollark: Do not embark on the madness of unsafe Rust. Not even the Rustonomicon can save you fully.

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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