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Cyanuric bromide

From Wikipedia, the free encyclopedia
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 mass317.766 g·mol−1
Melting point264.5 °C (508.1 °F; 537.6 K)[1]
Related compounds
Otheranions
Cyanuric fluoride;Cyanuric chloride
Related compounds
cyanogen bromideTribromoisocyanuric acid
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Cyanuric bromide is aheterocyclic compound with formula C3N3Br3. It contains a six-membered ring of alternatingnitrogen and carbon atoms, with abromine atom attached to each carbon. It is formed by the spontaneoustrimerisation ofcyanogen bromide.

Reactions

[edit]

Cyanuric bromide can be used to synthesize substitutedtriazines.[2] For example it reacts withanilines to form derivatives ofmelamine.[3] With ammonia,melamine is produced. Primary or secondary amines react.[1]Cyanuric trihydrazide is produced in the reaction withhydrazine.[1] When heated withurea at 140 °C,ammelide is formed.[1]

Cyanuric bromide reacts with water, particularly in alkaline conditions tocyanuric acid[4] andhydrogen bromide.[1]

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

Formation

[edit]

Cyanuric bromide can form in a reaction withpotassium ferrocyanide with bromine at 200 °C.[1] The trimerization reaction of cyanogen bromide (BrCN) is catalyzed byaluminium trichloride orhydrogen bromide.[1]

References

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  1. ^abcdefghSmolin, 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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