Cyanuric bromide is a

heterocyclic A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements as members of its ring(s). Heterocyclic organic chemistry is the branch of organic chemistry dealing with the synthesis, proper ...

compound with formula C₃N₃Br₃. It contains a six-membered ring of alternating

nitrogen Nitrogen is a chemical element; it has Symbol (chemistry), symbol N and atomic number 7. Nitrogen is a Nonmetal (chemistry), nonmetal and the lightest member of pnictogen, group 15 of the periodic table, often called the Pnictogen, pnictogens. ...

and carbon atoms, with a

bromine Bromine is a chemical element; it has chemical symbol, symbol Br and atomic number 35. It is a volatile red-brown liquid at room temperature that evaporates readily to form a similarly coloured vapour. Its properties are intermediate between th ...

atom attached to each carbon. It is formed by the spontaneous trimerisation of

cyanogen bromide Cyanogen bromide is the inorganic compound with the chemical formula, formula BrCN. It is a colorless solid that is widely used to modify biopolymers, fragment proteins and peptides (cuts the C-terminus of methionine), and synthesize other compo ...

. :

Reactions

Cyanuric bromide can be used to synthesize substituted triazines. For example it reacts with

aniline Aniline (From , meaning ' indigo shrub', and ''-ine'' indicating a derived substance) is an organic compound with the formula . Consisting of a phenyl group () attached to an amino group (), aniline is the simplest aromatic amine. It is an in ...

s to form derivatives of

melamine Melamine is an organic compound with the formula C3H6N6. This white solid is a trimer (chemistry), trimer of cyanamide, with a 1,3,5-Triazine, 1,3,5-triazine skeleton. Like cyanamide, it contains 66% nitrogen by mass, and its derivatives ha ...

. With ammonia,

is produced. Primary or secondary amines react. Cyanuric trihydrazide is produced in the reaction with

hydrazine Hydrazine is an inorganic compound with the chemical formula . It is a simple pnictogen hydride, and is a colourless flammable liquid with an ammonia-like odour. Hydrazine is highly hazardous unless handled in solution as, for example, hydraz ...

. When heated with

urea Urea, also called carbamide (because it is a diamide of carbonic acid), is an organic compound with chemical formula . This amide has two Amine, amino groups (–) joined by a carbonyl functional group (–C(=O)–). It is thus the simplest am ...

at 140 °C, ammelide is formed. Cyanuric bromide reacts with water, particularly in alkaline conditions to

cyanuric acid Cyanuric acid or 1,3,5-triazine-2,4,6-triol is a chemical compound with the chemical formula, formula (CNOH)3. Like many industrially useful chemicals, this triazine has many synonyms. This white, odorless solid finds use as a precursor or a com ...

and

hydrogen bromide Hydrogen bromide is the inorganic compound with the formula . It is a hydrogen halide consisting of hydrogen and bromine. A colorless gas, it dissolves in water, forming hydrobromic acid, which is saturated at 68.85% HBr by weight at room temper ...

. 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 Potassium hexacyanidoferrate(II) is the inorganic compound with formula K4 e(CN)6�3H2O. It is the potassium salt of the coordination complex e(CN)6sup>4−. This salt forms lemon-yellow monoclinic crystals. Synthesis In 1752, the French chemi ...

with bromine at 200 °C. The trimerization reaction of cyanogen bromide (BrCN) is catalyzed by aluminium trichloride or

References

{{Reflist Triazines Trimers (chemistry) Bromoarenes