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 chemistry is the branch of organic chemistry dealing with the synthesis, properties, and ...

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

nitrogen Nitrogen is the chemical element with the symbol N and atomic number 7. Nitrogen is a nonmetal and the lightest member of group 15 of the periodic table, often called the pnictogens. It is a common element in the universe, estimated at se ...

and carbon atoms, with a

bromine Bromine is a chemical element with the symbol Br and atomic number 35. It is the third-lightest element in group 17 of the periodic table ( halogens) and is a volatile red-brown liquid at room temperature that evaporates readily to form a simi ...

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

cyanogen bromide Cyanogen bromide is the inorganic compound with the formula (CN)Br or 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 compounds. ...

. :

Reactions

Cyanuric bromide can be used to synthesize substituted

triazine Triazines are a class of nitrogen-containing heterocycles. The parent molecules' molecular formula is . They exist in three isomeric forms, 1,3,5-triazines being common. Structure The triazines have planar six-membered benzene-like ring but ...

s. For example it reacts with

aniline Aniline is an organic compound with the formula C6 H5 NH2. Consisting of a phenyl group attached to an amino group, aniline is the simplest aromatic amine. It is an industrially significant commodity chemical, as well as a versatile starti ...

s to form derivatives of

melamine Melamine is an organic compound with the formula C3H6N6. This white solid is a trimer of cyanamide, with a 1,3,5-triazine skeleton. Like cyanamide, it contains 67% nitrogen by mass, and its derivatives have fire retardant properties due t ...

. With ammonia,

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

urea Urea, also known as carbamide, is an organic compound with chemical formula . This amide has two amino groups (–) joined by a carbonyl functional group (–C(=O)–). It is thus the simplest amide of carbamic acid. Urea serves an important ...

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 formula (CNOH)3. Like many industrially useful chemicals, this triazine has many synonyms. This white, odorless solid finds use as a precursor or a component of bleach ...

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 tempe ...

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

acetyl bromide Acetyl bromide is an acyl bromide compound. As is expected, it may be prepared by reaction between phosphorus tribromide and acetic acid: : 3 CH3COOH + PBr3 → 3 CH3COBr + H3PO3 As usual for an acid halide, acetyl bromide hydrolyzes rapidly i ...

is produced.

Formation

Cyanuric bromide can formed in a reaction with

potassium ferrocyanide Potassium ferrocyanide 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 chemist Pie ...

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

aluminium trichloride Aluminium chloride, also known as aluminium trichloride, is an inorganic compound with the formula . It forms hexahydrate with the formula , containing six water molecules of hydration. Both are colourless crystals, but samples are often conta ...

References

{{Reflist Triazines Organobromides