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2,4,6-Tribromoaniline is a brominated derivative of aniline with the formula C 6 H 4 Br 3 N. It is used in organic synthesis of pharmaceuticals, agrochemicals and fire-extinguishing agents. It is used in organic synthesis of pharmaceuticals, agrochemicals and fire-extinguishing agents.
Brominating aniline with elemental bromine gives 2,4,6-tribromoaniline. This is then diazotized, then reacted with ethanol to replace the diazonium group with hydrogen, forming 1,3,5-tribromobenzene. [3] It has also been prepared by these methods: [3] replacement of the amino group of 3,5-dibromoaniline with bromine
The bromoanilines form a group of three isomers where the bromine atom occupies the para, ortho or meta position on the aromatic ring. Bromoaniline isomers Arene substitution patterns. The three isomers are: 2-Bromoaniline (o-Bromoaniline) [1] 3-Bromoaniline (m-Bromoaniline) [2] 4-Bromoaniline (p-Bromoaniline) [3]
4-Bromoaniline is a compound where an aniline molecule is substituted with a bromine atom on the para position. Commercially available, this compound may be used as a building block, e.g. in the preparation of monobrominated biphenyl via the Gomberg-Bachmann reaction. [2]
For example, reaction of aniline with sulfuric acid at 180 °C produces sulfanilic acid, H 2 NC 6 H 4 SO 3 H. If bromine water is added to aniline, the bromine water is decolourised and a white precipitate of 2,4,6-tribromoaniline is formed. To generate the mono-substituted product, a protection with acetyl chloride is required:
The reaction details following the usual patterns of electrophilic aromatic substitution: RC 6 H 5 + Br 2 → RC 6 H 4 Br + HBr. A prominent application of this reaction is the production of tetrabromobisphenol-A from bisphenol-A. Free-radical substitution with bromine is commonly used to prepare organobromine compounds.
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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.