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
Preferred IUPAC name 2,4,6-Tribromophenol
Other names Tribromophenol; 2,4,6-TBP; TBP
Identifiers
CAS Number	118-79-6 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:47696 N
ChEMBL	ChEMBL220087 Y
ChemSpider	1438 Y
DrugBank	DB02417 Y
ECHA InfoCard	100.003.890
KEGG	C14454 Y
PubChem CID	1483
UNII	YS6K3EU393 Y
CompTox Dashboard (EPA)	DTXSID6021959
InChI InChI=1S/C6H3Br3O/c7-3-1-4(8)6(10)5(9)2-3/h1-2,10H Y Key: BSWWXRFVMJHFBN-UHFFFAOYSA-N Y 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[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]
Solubility in water	Slightly soluble[1] 59-61 mg/L[3]
Hazards
GHS labelling:
Pictograms	[4]
NFPA 704 (fire diamond)	2 0 0
Lethal dose or concentration (LD, LC):
LD50 (median dose)	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^{[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]}