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2,4,6-Tribromoaniline can be prepared by treating bromine water with aniline in a solution of acetic acid or dilute hydrochloric acid: [1] By reacting bromine with aniline in water, a white precipitate immediately forms and that is 2,4,6-tribromoaniline
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
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 .
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]
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.
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For example, p-bromobiphenyl may be prepared from 4-bromoaniline and benzene: [4] BrC 6 H 4 NH 2 + C 6 H 6 → BrC 6 H 4 −C 6 H 5. The reaction offers a wide scope for both diazonium component and arene component but yields are generally low following the original procedure (less than 40%), given the many side-reactions of diazonium salts.