cyanuric bromide
{{Chembox
| IUPACName = 2,4,6-tribromo-1,3,5-triazine
| ImageFile = Cyanuric bromide.png
|Section1={{Chembox Identifiers
| ChemSpiderID = 25112
| PubChem = 26967
| DTXSID = DTXSID90274819
| CASNo = 14921-00-7
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = F6S2VES5UF
| StdInChI=1S/C3Br3N3/c4-1-7-2(5)9-3(6)8-1
| StdInChIKey = VHYBUUMUUNCHCK-UHFFFAOYSA-N
| SMILES = C1(=NC(=NC(=N1)Br)Br)Br
}}
|Section2={{Chembox Properties
|C=3|N=3|Br=3
| MeltingPtC=264.5
}}
|Section7={{Chembox Hazards
}}
|Section8={{Chembox Related
| OtherAnions = Cyanuric fluoride; Cyanuric chloride
| OtherCompounds = cyanogen bromide Tribromoisocyanuric acid
}}
}}
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.{{cite book |title=Houben-Weyl Methods of Organic Chemistry Vol. E 9c, 4th Edition Supplement: Hetarenes III |date=2014 |publisher=Georg Thieme Verlag |isbn=978-3-13-181514-9 |page=754 |url=https://books.google.com/books?id=7i-GAwAAQBAJ&pg=PA754 |language=en}} For example it reacts with anilines to form derivatives of melamine.{{cite journal |last1=Kurzer |first1=Frederick |title=639. Cyanamides. Part III. The formation of substituted triazines from o-halogenophenylureas and arylsulphonyl chlorides |journal=Journal of the Chemical Society (Resumed) |date=1949 |pages=3033 |doi=10.1039/JR9490003033}} 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{{cite book |last1=Wells |first1=Alexander Frank |title=Structural Inorganic Chemistry |date=2012 |publisher=OUP Oxford |isbn=978-0-19-965763-6 |page=931 |url=https://books.google.com/books?id=uR77AAAAQBAJ&pg=PA931 |language=en}} 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.