2,4,6-Tribromophenol

2,4,6-Tribromophenol
Names
	Preferred IUPAC name 2,4,6-Tribromophenol
	Other names Tribromophenol; 2,4,6-TBP; TBP
Identifiers
CAS Number	118-79-6 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:47696 ;
ChEMBL	ChEMBL220087 ;
ChemSpider	1438 ;
DrugBank	DB02417 ;
ECHA InfoCard	100.003.890
KEGG	C14454 ;
PubChem CID	1483;
UNII	YS6K3EU393 ;
CompTox Dashboard (EPA)	DTXSID6021959 ;
	InChI InChI=1S/C6H3Br3O/c7-3-1-4(8)6(10)5(9)2-3/h1-2,10H Key: BSWWXRFVMJHFBN-UHFFFAOYSA-N ; InChI=1/C6H3Br3O/c7-3-1-4(8)6(10)5(9)2-3/h1-2,10H Key: BSWWXRFVMJHFBN-UHFFFAOYAF;
	SMILES Brc1cc(Br)cc(Br)c1O;
Properties
Chemical formula	C6H3Br3O
Molar mass	330.801 g·mol−1
Appearance	White needles or prisms
Melting point	95.5 °C (203.9 °F; 368.6 K)
Boiling point	244 °C (471 °F; 517 K); 286 °C
Solubility in water	Slightly soluble; 59-61 mg/L
Hazards
	GHS labelling:
Pictograms
NFPA 704 (fire diamond)	2 0 0
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	2000 mg/kg (rat, oral)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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,^[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]

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.^[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

^ ^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
^ ^a ^b ^c Concise International Chemical Assessment Document 66: 2,4,6-Tribromophenol and Other Simple Brominated Phenols, International Programme on Chemical Safety
^ ^a ^b Merck Index, 11th Edition, 9526
^ Sigma-Aldrich Co., 2,4,6-Tribromophenol. Retrieved on 2015-02-19.
^ 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.
^ "2,4,6 Tribromophenol" (PDF). ICL Industrial Products. Archived from the original (PDF) on August 27, 2019. Retrieved April 13, 2022.
^ Tsunoda K, Takahashi M (1989). "Laboratory Evaluation of Chemicals as Wood Prerservatives: (1) Tribromophenol" (PDF). Wood Research. 76. Kyoto University: 39–48.
^ "MeSH Browser". meshb.nlm.nih.gov. Retrieved 2019-08-27.
^ 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.
^ 38,000 more bottles of Lipitor recalled over odor complaints, CNN.com, October 30, 2010
^ Lipitor (atorvastatin) 40 mg: Recall Specific Bottles, drugs.com, Dec 23, 2010
^ Tylenol Recall Expands, WebMD Health News, January 18, 2010
^ McNeil Consumer Healthcare Announces Voluntary Recall Of One Product Lot Of TYLENOL Extra Strength Caplets 225 Count Distributed In The U.S.

[Gardner-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

[Inchem-2] Concise International Chemical Assessment Document 66: 2,4,6-Tribromophenol and Other Simple Brominated Phenols, International Programme on Chemical Safety

[Merck-3] Merck Index, 11th Edition, 9526

[sigma-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

[WebMd-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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