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Revision as of 17:00, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 443344821 of page 2,4,6-Tribromoanisole for the Chem/Drugbox validation project (updated: 'CASNo').		Latest revision as of 08:58, 29 November 2024 edit DMacks (talk | contribs)Edit filter managers, Autopatrolled, Administrators186,372 edits alt
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			{{redirect|2,4,6-TBA|2,4,6-trichlorobenzoic acid|2,4,6-Trichlorobenzoyl chloride}}
	{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
	{{chembox		{{chembox
			| Verifiedfields = changed
⚫	| verifiedrevid = 443342532
			| Watchedfields = changed
	|Reference=<ref> at ]</ref>
		⚫	| verifiedrevid = 477210687
⚫	|ImageFile=2,4,6-tribromoanisole.png
			| Reference =<ref>{{cite web |url=https://www.sigmaaldrich.com/US/en/product/aldrich/398780|title=2,4,6-Tribromoanisole |website=]}}</ref>
⚫	|ImageSize=150px
		⚫	| ImageFile =2,4,6-tribromoanisole.svg
⚫	|IUPACName=1,3,5-Tribromo-2-methoxybenzene
		⚫	| ImageSize =150px
⚫	|OtherNames=Tribromoanisole; TBA
			| ImageAlt = Skeletal formula of 2,4,6-tribromoanisole
			| ImageFile1 = 2,4,6-Tribromoanisole-3D-balls.png
			| ImageSize1 = 160
			| ImageAlt1 = Ball-and-stick model of the 2,4,6-tribromoanisole molecule
		⚫	| PIN =1,3,5-Tribromo-2-methoxybenzene
		⚫	| OtherNames =Tribromoanisole; TBA
	|Section1={{Chembox Identifiers		|Section1={{Chembox Identifiers
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
		⚫	| ChemSpiderID = 21170966
⚫	| ChEBI_Ref = {{ebicite|correct|EBI}}
			| InChI = 1/C7H5Br3O/c1-11-7-5(9)2-4(8)3-6(7)10/h2-3H,1H3
	| ChEBI = 38703
		⚫	| SMILES1 = COc1c(Br)cc(Br)cc1Br
⚫	| ChemSpiderID = 11345
		⚫	| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
	| InChI = 1/C10H12O3/c1-7(2)13-10(12)8-5-3-4-6-9(8)11/h3-7,11H,1-2H3
		⚫	| StdInChI = 1S/C7H5Br3O/c1-11-7-5(9)2-4(8)3-6(7)10/h2-3H,1H3
	| InChIKey = YEULQIJMIOWCHB-UHFFFAOYAR
		⚫	| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
⚫	| SMILES1 = O=C(OC(C)C)c1ccccc1O
		⚫	| StdInChIKey = YXTRCOAFNXQTKL-UHFFFAOYSA-N
⚫	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
			| CASNo_Ref = {{cascite|changed|??}}
⚫	| StdInChI = 1S/C10H12O3/c1-7(2)13-10(12)8-5-3-4-6-9(8)11/h3-7,11H,1-2H3
			| CASNo =607-99-8
⚫	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
			| PubChem =11839
⚫	| StdInChIKey = YEULQIJMIOWCHB-UHFFFAOYSA-N
		⚫	| UNII_Ref = {{fdacite|correct|FDA}}
	| CASNo = <!-- blanked - oldvalue: 607-99-8 -->
	| PubChem=11839
	| UNII_Ref = {{fdacite|correct|FDA}}
	| UNII = DO7M3M4LX5		| UNII = DO7M3M4LX5
	| SMILES=COC1=C(C=C(C=C1Br)Br)Br		| SMILES =COC1=C(C=C(C=C1Br)Br)Br
	}}		}}
	|Section2={{Chembox Properties		|Section2={{Chembox Properties
			| C=7 | H=5 | Br=3 | O=1
	| Formula=C<sub>7</sub>H<sub>5</sub>Br<sub>3</sub>O
			| Appearance =
	| MolarMass=344.826
			| Density =
	| Appearance=
			| MeltingPtC = 84 to 88
	| Density=
			| MeltingPt_notes =
	| MeltingPt=84-88 °C
	| BoilingPt=297-299 °C		| BoilingPtC = 297 to 299
			| BoilingPt_notes =
	| Solubility=
			| Solubility =
	}}		}}
	|Section3={{Chembox Hazards		|Section3={{Chembox Hazards
	| MainHazards=		| MainHazards =
	| FlashPt=		| FlashPt =
			| AutoignitionPt =
	| Autoignition=
	}}		}}
	}}		}}
			'''2,4,6-Tribromoanisole''' ('''TBA''') is a chemical compound that is a ] derivative of ]. It is one of the chemicals responsible for ].<ref>{{cite journal |doi=10.1021/jf030632f |journal=J Agric Food Chem |year=2004 |volume=52 |issue=5 |pages=1255–1262 |title=Identification and responsibility of 2,4,6-tribromoanisole in musty, corked odors in wine |vauthors=Chatonnet P, Bonnet S, Boutou S, Labadie MD |pmid=14995130}}</ref>
			Tribromoanisole is a fungal ] of ], which is used as a fungicide. It can be found in minute traces on packaging materials stored in the presence of fiberboard treated with 2,4,6-tribromophenol. These traces can cause an unpleasant mustiness in packaged foods.<ref>{{cite journal |title=2,4,6-Tribromoanisole: a Potential Cause of Mustiness in Packaged Food |author1=Whitfield, Frank B. |author2=Hill, Jodie L. |author3=Shaw, Kevin J. |journal=J. Agric. Food Chem. |year=1997 |volume=45 |issue=3 |pages=889–893 |doi=10.1021/jf960587u}}</ref>
			Tribromoanisole is usually produced when naturally occurring airborne ] or ] (usually '']'' sp., '']'' sp., '']'', '']'', '']'' sp., or '']'') are presented with ], which they then convert into ] derivatives. The bromophenols can originate from various contaminants including those found in some ]s and wood ]s. They can also migrate from other objects such as shipping pallets treated by bromophenols.
			Tribromoanisole has a very low ]. It is 0.08-0.3 parts per trillion (ppt) in water and 2-6 ppt in wine<ref>{{Cite web |url=http://www.restek.com/Technical-Resources/Technical-Library/General-Interest/general_A031 |title=Fast Screening of Recalled Tylenol for Tribromoanisole and Related Adulterants Using QuEChERS and GC-TOFMS |first1=Jason |last1=Thomas |first2=Jack |last2=Cochran |name-list-style=amp |date=2010 |website=Restek Corporation |access-date=June 29, 2011 |archive-date=July 27, 2017 |archive-url=https://web.archive.org/web/20170727065722/http://www.restek.com/Technical-Resources/Technical-Library/General-Interest/general_A031 |url-status=dead}}</ref> (or 3.4-7.9 ng/L<ref>{{cite web |url=http://www.wawgg.org/files/documents/THK_&_Richard_Larsen_Tasting_Room_Training_power_point.pdf |title=WAWGG Annual Meeting 2011: Tasting Room Staff Training |first1=Thomas |last1=Henick-Kling |first2=Richard |last2=Larsen |name-list-style=amp |website=Washington Association of Wine Grape Growers |url-status=dead |archive-url=https://web.archive.org/web/20110929213420/http://www.wawgg.org/files/documents/THK_&_Richard_Larsen_Tasting_Room_Training_power_point.pdf |archive-date=September 29, 2011}}</ref>) so even very minute amounts can be detected. It causes unpleasant earthy, musty and moldy aromas.
			==Consumer product recalls==
			There have been several events in which consumer products were recalled due to odors caused by tribromoanisole on product packaging. In 2010 and 2011, ] voluntarily recalled some ] products, including ], due to an odor caused by tribromoanisole.<ref name=WebMd>{{cite web |url=http://arthritis.webmd.com/news/20091229/tylenol-recall-expands |title=Tylenol Recall Expands |first=Daniel J. |last=DeNoon |date=December 29, 2009 |website=WebMD Health News}}</ref><ref>{{cite web |url=https://www.fda.gov/Safety/Recalls/ucm261498.htm/ |title=McNeil Consumer Healthcare Announces Voluntary Recall Of One Product Lot Of TYLENOL Extra Strength Caplets 225 Count Distributed In The U.S. |date=June 28, 2011 |website=] |url-status=dead |archive-url=https://web.archive.org/web/20111103033823/https://www.fda.gov/Safety/Recalls/ucm261498.htm/ |archive-date=November 3, 2011}}</ref> In this case, a supplier had used ] to treat wooden ]s on which product packaging materials were transported and stored.<ref name=WebMd/> In 2010 and in 2011, ] recalled bottles of ] after reports of an odor linked to the packaging bottles.<ref>{{cite web |url=http://www.cnn.com/2010/HEALTH/10/30/lipitor.recall/ |title=38,000 more bottles of Lipitor recalled over odor complaints |date=October 30, 2010 |website=]}}</ref> Pfizer said the bottles were supplied by a third-party manufacturer and determined the cause to be exposure of the bottles to low levels of tribromoanisole as they were shipped or stored.<ref>{{cite web |url=https://www.drugs.com/fda/lipitor-atorvastatin-40-mg-recall-specific-bottles-12873.html |title=Lipitor (atorvastatin) 40 mg: Recall Specific Bottles |date=December 23, 2010 |website=]}}</ref>
			==See also==
			* ]
			==References==
			{{reflist}}
			{{DEFAULTSORT:Tribromoanisole, 2,4,6-}}
			]
			]