| Revision as of 17:01, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 476654884 of page 2,4,6-Tribromophenol for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 13:24, 16 February 2024 edit Marbletan (talk | contribs)Extended confirmed users5,256 edits →Production: 2,4,6-Tribromphenol Reaktionsschemata.svg |
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{{cs1 config|name-list-style=vanc}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| ImageFileL1=2,4,6-Tribromophenol.png |
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| verifiedrevid = 477210750 |
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| ImageFileR1=2,4,6-Tribromophenol-3D-balls.png |
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| ImageFileL1 =2,4,6-Tribromophenol.png |
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| ImageFileR1 =2,4,6-Tribromophenol-3D-balls.png |
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| IUPACName=2,4,6-Tribromophenol |
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| PIN =2,4,6-Tribromophenol |
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| OtherNames=Tribromophenol; 2,4,6-TBP; TBP |
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| OtherNames =Tribromophenol; 2,4,6-TBP; TBP |
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| Section1={{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 1438 |
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| ChemSpiderID = 1438 |
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| StdInChIKey = BSWWXRFVMJHFBN-UHFFFAOYSA-N |
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| StdInChIKey = BSWWXRFVMJHFBN-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo=118-79-6 |
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| CASNo =118-79-6 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| PubChem=1483 |
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| UNII = YS6K3EU393 |
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| PubChem =1483 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 47696 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = DB02417 |
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| DrugBank = DB02417 |
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| SMILES = Brc1cc(Br)cc(Br)c1O |
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| SMILES = Brc1cc(Br)cc(Br)c1O |
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| C=6|H=3|Br=3|O=1 |
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| C=6 | H=3 | Br=3 | O=1 |
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| Appearance=White needles or prisms<ref name=Gardner>"'''3851''': Tribromophenol" in ''Gardner's Commercially Important Chemicals: Synonyms, Trade Names, and Properties'', G. W. A. Milne (Editor), ISBN 978-0471735182, page 632</ref> |
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| Appearance =White needles or prisms<ref name=Gardner>"'''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</ref> |
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| MeltingPtC = 95.5 |
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| MeltingPt=95.5 °C<ref name=Gardner/> |
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| BoilingPt=244 °C<ref name="Merck">'']'', 11th Edition, '''9526'''</ref><br>286 °C<ref name=Gardner/> |
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| BoilingPtC = 244 |
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| Solubility=Slightly soluble<ref name=Gardner/><br>59-61 mg/L<ref name=Inchem>, International Programme on Chemical Safety</ref> |
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| BoilingPt_ref = <ref name="Merck">'']'', 11th Edition, '''9526'''</ref><br />286 °C<ref name=Gardner/> |
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| Solubility =Slightly soluble<ref name=Gardner/><br />59-61 mg/L<ref name=Inchem>, International Programme on Chemical Safety</ref> |
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| LD50 = 2000 mg/kg (rat, oral)<ref name=Gardner/> |
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| LD50 = 2000 mg/kg (rat, oral)<ref name=Gardner/> |
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| GHSPictograms = {{GHS07}}{{GHS09}}<ref name="sigma">{{Sigma-Aldrich|Fluka|id=137715|name=2,4,6-Tribromophenol|accessdate=2015-02-19}}</ref> |
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| NFPA-H = 2 |
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| NFPA-F = 0 |
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| NFPA-R = 0 |
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'''2,4,6-Tribromophenol''' (TBP) is a ] derivative of ]. It is used as a ], as a wood preservative, and an intermediate in the preparation of ]s. |
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== Production == |
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Although natural TBP has been identified in ocean sediments as a metabolite of marine fauna,<ref>{{cite journal | doi = 10.1002/etc.5620200407 |vauthors=Fielman KT, Woodin SA, Lincoln DE | year = 2001 | title = Polychaete indicator species as a source of natural halogenated organic compounds in marine sediments | journal = Environmental Toxicology and Chemistry | volume = 20 | issue = 4 | pages = 738–747 | pmid = 11345448|s2cid=42911887 }}</ref> 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.<ref name=Inchem/> TBP can be prepared by the controlled reaction of elemental bromine with phenol:<ref name="Merck"/> |
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: ]{{clear-left}} |
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== Uses == |
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The predominant use of TBP is as an intermediate in the preparation of flame retardants such as brominated ]s.<ref name=Inchem/> TBP is reacted with ] to form the ] ], which is used as a fungicide and wood preservative.<ref>{{cite web |title=2,4,6 Tribromophenol |url=https://www.icl-ip.com/wp-content/uploads/2012/01/613WoodpreservativeICLIP.pdf |website=ICL Industrial Products |access-date=April 13, 2022 |archive-url=https://web.archive.org/web/20190827095054/https://www.icl-ip.com/wp-content/uploads/2012/01/613WoodpreservativeICLIP.pdf |archive-date=August 27, 2019 |url-status=dead}}</ref><ref>{{cite journal |last1=Tsunoda |first1=Kunio |last2=Takahashi |first2=Munezoh |title=Laboratory Evaluation of Chemicals as Wood {{not a typo|Prerservatives}}: (1) Tribromophenol |journal=Wood Research |date=1989 |publisher=Kyoto University |volume=76 |pages=39{{endash}}48 |url=https://core.ac.uk/download/pdf/39187475.pdf}}</ref> |
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=== Bismuth salt === |
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The ] salt is the active ingredient in Xeroform{{clarify|date=August 2021}} ].<ref>{{Cite web|url=https://meshb.nlm.nih.gov/#/record/ui?ui=C004554|title=MeSH Browser|website=meshb.nlm.nih.gov|access-date=2019-08-27}}</ref> |
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== Metabolism == |
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Microbial metabolism in products treated with TBP is known to produce ] (TBA),<ref>{{cite journal | title = 2,4,6-Tribromoanisole: a Potential Cause of Mustiness in Packaged Food |author1=Frank B. Whitfield |author2=Jodie L. Hill |author3=Kevin J. Shaw | journal = J. Agric. Food Chem. | year = 1997 | volume = 45 | issue = 3 | pages = 889–893 | doi = 10.1021/jf960587u}}</ref> which has a musty odor. In 2010 and 2011, ] and ] voluntarily recalled some products due to TBA odors from wooden pallets which were treated with TBP.<ref>, CNN.com, October 30, 2010</ref><ref>, drugs.com, Dec 23, 2010</ref><ref name=WebMd>, WebMD Health News, January 18, 2010</ref><ref></ref> |
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== References == |
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{{reflist}} |
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{{DEFAULTSORT:Tribromophenol, 2, 4, 6-}} |
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] |
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] |
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] |