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 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
CAS Number	645-92-1
3D model (JSmol)	Interactive image
ChEBI	CHEBI:28646
ChemSpider	12063
ECHA InfoCard	100.010.415
KEGG	C08733
PubChem CID	12583
UNII	LC8G9556Q0
CompTox Dashboard (EPA)	DTXSID3060950
InChI InChI=1S/C3H5N5O/c4-1-6-2(5)8-3(9)7-1/h(H5,4,5,6,7,8,9) Key: MASBWURJQFFLOO-UHFFFAOYSA-N InChI=1/C3H5N5O/c4-1-6-2(5)8-3(9)7-1/h(H5,4,5,6,7,8,9) Key: MASBWURJQFFLOO-UHFFFAOYAL
SMILES O=C\1/N=C(/N)NC(=N/1)/N
Properties
Chemical formula	C3H5N5O
Molar mass	127.107 g·mol^−1
Appearance	White powder
Melting point	N/A (decomposes before melting)
Solubility in water	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.