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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
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 .
Industrially, it is mainly produced by the reaction of hydrogen gas with bromine gas at 200–400 °C with a platinum catalyst. However, reduction of bromine with red phosphorus is a more practical way to produce hydrogen bromide in the laboratory: [2] 2 P + 6 H 2 O + 3 Br 2 → 6 HBr + 2 H 3 PO 3 H 3 PO 3 + H 2 O + Br 2 → 2 HBr + H 3 PO 4
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.
NBr 3 can be produced by the reaction of bromine or hypobromite and ammonia in a dilute aqueous buffer solution. [3] It can also be prepared by the reaction of bromine and bromine azide. [4] Ammonia and bromine undergo glow discharge, and after treatment, red NBr 3 ·6NH 3 can be obtained. [5] Pure nitrogen NBr 3 was only produced in 1975. [6]
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.