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2,4,6-Tribromophenol
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2,4,6-Tribromophenol

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2,4,6-Tribromophenol
2,4,6-Tribromophenol.png
2,4,6-Tribromophenol-3D-balls.png
Names
Preferred 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
PubChem CID
UNII
  • InChI=1S/C6H3Br3O/c7-3-1-4(8)6(10)5(9)2-3/h1-2,10H checkY
    Key: BSWWXRFVMJHFBN-UHFFFAOYSA-N checkY
  • 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 330.801 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
Slightly soluble
59-61 mg/L
Hazards
GHS labelling:
GHS07: Exclamation markGHS09: Environmental hazard
NFPA 704 (fire diamond)
2
0
0
Lethal dose or concentration (LD, LC):
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).
☒N verify (what is checkY☒N ?)

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, 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. TBP can be prepared by the controlled reaction of elemental bromine with phenol:

2,4,6-tribromophenol synthesis.PNG

Uses

The predominant use of TBP is as an intermediate in the preparation of flame retardants such as brominated epoxy resins. 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 Xeroformdressing.

Metabolism

Microbial metabolism in products treated with TBP is known to produce 2,4,6-tribromoanisole (TBA), 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.


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