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Cyanuric bromide

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Cyanuric bromide
Names
IUPAC name 2,4,6-tribromo-1,3,5-triazine
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C3Br3N3/c4-1-7-2(5)9-3(6)8-1Key: VHYBUUMUUNCHCK-UHFFFAOYSA-N
SMILES
  • C1(=NC(=NC(=N1)Br)Br)Br
Properties
Chemical formula C3Br3N3
Molar mass 317.766 g·mol
Melting point 264.5 °C (508.1 °F; 537.6 K)
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 , 100 kPa). Infobox references
Chemical compound

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. For example it reacts with anilines to form derivatives of melamine. 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 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.

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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