Cyanuric bromide explained

Cyanuric bromide is a heterocyclic compound with formula C3N3Br3. It contains a six-membered ring of alternating nitrogen and carbon atoms, with a bromine atom attached to each carbon. It is formed by the spontaneous trimerisation of cyanogen bromide.

Reactions

Cyanuric bromide can be used to synthesize substituted triazines.[1] For example it reacts with anilines to form derivatives of melamine.[2] With ammonia, melamine is produced. Primary or secondary amines react. Cyanuric trihydrazide is produced in the reaction with hydrazine. When heated with urea at 140 °C, ammelide is formed.

Cyanuric bromide reacts with water, particularly in alkaline conditions to cyanuric acid[3] and hydrogen bromide.

Cyanuric bromide can add bromine to other compounds and when it is heated with acetic acid, acetyl bromide is produced.

Formation

Cyanuric bromide can form in a reaction with potassium ferrocyanide with bromine at 200 °C. The trimerization reaction of cyanogen bromide (BrCN) is catalyzed by aluminium trichloride or hydrogen bromide.

Notes and References

  1. Book: Houben-Weyl Methods of Organic Chemistry Vol. E 9c, 4th Edition Supplement: Hetarenes III . 2014 . Georg Thieme Verlag . 978-3-13-181514-9 . 754 . en.
  2. Kurzer . Frederick . 639. Cyanamides. Part III. The formation of substituted triazines from o-halogenophenylureas and arylsulphonyl chlorides . Journal of the Chemical Society (Resumed) . 1949 . 3033 . 10.1039/JR9490003033.
  3. Book: Wells . Alexander Frank . Structural Inorganic Chemistry . 2012 . OUP Oxford . 978-0-19-965763-6 . 931 . en.