Cyanuric bromide

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.

Cyanuric bromide
Names
IUPAC name
2,4,6-tribromo-1,3,5-triazine
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C3Br3N3/c4-1-7-2(5)9-3(6)8-1
    Key: VHYBUUMUUNCHCK-UHFFFAOYSA-N
  • C1(=NC(=NC(=N1)Br)Br)Br
Properties
C3Br3N3
Molar mass 317.766 g·mol−1
Melting point 264.5 °C (508.1 °F; 537.6 K)[1]
Related compounds
Other anions
 Cyanuric fluoride; Cyanuric chloride
Related compounds
 cyanogen bromide Tribromoisocyanuric acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Reactions

Cyanuric bromide can be used to synthesize substituted triazines.[2] For example it reacts with anilines to form derivatives of melamine.[3] With ammonia, melamine is produced. Primary or secondary amines react.[1] Cyanuric trihydrazide is produced in the reaction with hydrazine.[1] When heated with urea at 140 °C, ammelide is formed.[1]

Cyanuric bromide reacts with water, particularly in alkaline conditions to cyanuric acid[4] and hydrogen bromide.[1]

Cyanuric bromide can add bromine to other compound, and when it is heated with acetic acid, acetyl bromide is produced.[1]

Formation

Cyanuric bromide can formed in a reaction with potassium ferrocyanide with bromine at 200 °C.[1] The trimerization reaction of cyanogen bromide (BrCN) is catalyzed by aluminium trichloride or hydrogen bromide.[1]

References
  1. Smolin, Edwin M.; Rapoport, Lorence (2009). s-Triazines and Derivatives. John Wiley & Sons. pp. 62–65. ISBN 978-0-470-18812-5.
  2. Houben-Weyl Methods of Organic Chemistry Vol. E 9c, 4th Edition Supplement: Hetarenes III. Georg Thieme Verlag. 2014. p. 754. ISBN 978-3-13-181514-9.
  3. Kurzer, Frederick (1949). "639. Cyanamides. Part III. The formation of substituted triazines from o-halogenophenylureas and arylsulphonyl chlorides". Journal of the Chemical Society (Resumed): 3033. doi:10.1039/JR9490003033.
  4. Wells, Alexander Frank (2012). Structural Inorganic Chemistry. OUP Oxford. p. 931. ISBN 978-0-19-965763-6.
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