2,4,6-Tribromophenol

2,4,6-Tribromophenol
Names
	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;
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	class="wikitable collapsible" style="min-width: 50em;"

Production

Although natural TBP has been identified in ocean sediments as a metabolite of marine fauna,^[6] 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.

Bismuth salt

The bismuth salt is the active ingredient in Xeroform dressing.^[7]

Metabolism

Microbial metabolism in products treated with TBP is known to produce 2,4,6-tribromoanisole (TBA),^[8] 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.^[9]^[10]^[11]^[12]

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
^ ^a ^b "Globally Harmonized System of Classification and Labelling of Chemicals" (pdf). 2021. Annex 3: Codification of Statements and Pictograms (pp 268–385).
^ 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.
^ https://www.nlm.nih.gov/cgi/mesh/2008/MB_cgi?field=uid&term=C004554
^ 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

[GHS2021_annex-3-4] "Globally Harmonized System of Classification and Labelling of Chemicals" (pdf). 2021. Annex 3: Codification of Statements and Pictograms (pp 268–385).

[sigma-5] Sigma-Aldrich Co., 2,4,6-Tribromophenol. Retrieved on 2015-02-19.

[6] 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.

[7] ttps://www.nlm.nih.gov/cgi/mesh/2008/MB_cgi?field=uid&term=C004554

[8] 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.

[9] 38,000 more bottles of Lipitor recalled over odor complaints, CNN.com, October 30, 2010

[10] Lipitor (atorvastatin) 40 mg: Recall Specific Bottles, drugs.com, Dec 23, 2010

[WebMd-11] Tylenol Recall Expands, WebMD Health News, January 18, 2010

[12] McNeil Consumer Healthcare Announces Voluntary Recall Of One Product Lot Of TYLENOL® Extra Strength Caplets 225 Count Distributed In The U.S.

[1]

[3]

[2]

[4]

[5]

[6]

[7]

[8]

[9]

[10]

[11]

[12]

Code	Symbol description	Image link
GHS01	{{GHS exploding bomb}}	Image:GHS-pictogram-explos.svg	Explosive
GHS02	{{GHS flame}}	Image:GHS-pictogram-flamme.svg
GHS03	{{GHS flame over circle}}	Image:GHS-pictogram-rondflam.svg
GHS04	{{GHS gas cylinder}}	Image:GHS-pictogram-bottle.svg
GHS05	{{GHS corrosion}}	Image:GHS-pictogram-acid.svg	Corrosive
GHS06	{{GHS skull and crossbones}}	Image:GHS-pictogram-skull.svg	Accute Toxic
GHS07	{{GHS exclamation mark}}	Image:GHS-pictogram-exclam.svg	Irritant
GHS08	{{GHS health hazard}}	Image:GHS-pictogram-silhouette.svg	Health Hazard
GHS09	{{GHS environment}}	Image:GHS-pictogram-pollu.svg	Environment