2,4,6-Tribromoanisole

2,4,6-Tribromoanisole
Names
	Preferred IUPAC name 1,3,5-Tribromo-2-methoxybenzene
	Other names Tribromoanisole; TBA
Identifiers
CAS Number	607-99-8 ;
3D model (JSmol)	Interactive image; Interactive image;
ChemSpider	21170966 ;
ECHA InfoCard	100.156.226
PubChem CID	11839;
UNII	DO7M3M4LX5 ;
CompTox Dashboard (EPA)	DTXSID1060558 ;
	InChI InChI=1S/C7H5Br3O/c1-11-7-5(9)2-4(8)3-6(7)10/h2-3H,1H3 Key: YXTRCOAFNXQTKL-UHFFFAOYSA-N ; InChI=1/C7H5Br3O/c1-11-7-5(9)2-4(8)3-6(7)10/h2-3H,1H3;
	SMILES COC1=C(C=C(C=C1Br)Br)Br; COc1c(Br)cc(Br)cc1Br;
Properties
Chemical formula	C7H5Br3O
Molar mass	344.828 g·mol−1
Melting point	84 to 88 °C (183 to 190 °F; 357 to 361 K)
Boiling point	297 to 299 °C (567 to 570 °F; 570 to 572 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

2,4,6-Tribromoanisole (TBA) is a chemical compound that is a brominated derivative of anisole. It is one of the chemicals responsible for cork taint.

Tribromoanisole is a fungal metabolite of 2,4,6-tribromophenol, 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.

Tribromoanisole is usually produced when naturally occurring airborne fungi or bacteria (usually Aspergillus sp., Penicillium sp., Actinomycetes, Botrytis cinerea, Rhizobium sp., or Streptomyces) are presented with brominated phenolic compounds, which they then convert into bromoanisole derivatives. The bromophenols can originate from various contaminants including those found in some pesticides and wood preservatives. They can also migrate from other objects such as shipping pallets treated by bromophenols.

Tribromoanisole has a very low odor detection threshold. It is 0.08-0.3 parts per trillion (ppt) in water and 2-6 ppt in wine (or 3.4-7.9 ng/L) so even very minute amounts can be detected. It causes unpleasant earthy, musty and moldy aromas.

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