Ammeline

Ammeline (4,6-diamino-2-hydroxy-1,3,5-triazine) is a triazine derivative. It is the hydrolysis product of melamine.

Ammeline
Structural formula
Structural formula
Ball-and-stick model
Ball-and-stick model
Names
Preferred IUPAC name
4,6-Diamino-1,3,5-triazin-2-ol
Other names
2,4-Diamino-6-hydroxy-1,3,5-triazine
4,6-Diamino-2-hydroxy-1,3,5-triazine
4,6-diamino-1,3,5-triazin-2(1H)-one
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.010.415
KEGG
UNII
  • InChI=1S/C3H5N5O/c4-1-6-2(5)8-3(9)7-1/h(H5,4,5,6,7,8,9) checkY
    Key: MASBWURJQFFLOO-UHFFFAOYSA-N checkY
  • InChI=1/C3H5N5O/c4-1-6-2(5)8-3(9)7-1/h(H5,4,5,6,7,8,9)
    Key: MASBWURJQFFLOO-UHFFFAOYAL
  • O=C\1/N=C(/N)NC(=N/1)/N
Properties
C3H5N5O
Molar mass 127.107 g·mol−1
Appearance White powder
Melting point N/A (decomposes before melting)
Trace
Solubility Soluble in aqueous alkalies and mineral acids, but not acetic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Synthesis

Ammeline can be synthesized by the pyrolysis of urea or the condensation reaction among 2 moles of dicyandiamide and 1 mole of biuret.

2 C2H4N4 + C2H5N3O2 → 2C3H5N5O + NH3

Chemical properties

Ammeline is weakly acidic with pKa ~9. It can form nitrate, sulfate, chromate, and oxalate salts. Ammeline reacts with boiling dilute hydrochloric acid to form melem and ammonia.

Ammeline is the first step in melamine hydrolysis. Further hydrolysis (e.g. boiling ammeline with dilute alkali) yields ammelide.

References
  • B. Bann and S.A. Miller (1958). "Melamines and derivatives of melamine". Chemical Reviews. 58: 131–172. doi:10.1021/cr50019a004.
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