Ammeline

Ammeline

Names
IUPAC name 4,6-Diamino-2-hydroxy-1,3,5-triazine
Other names Ammelin, s-triazin-2-ol, 2,4-diamino-1,3,5-triazin-6-one
Identifiers
CAS Registry Number	645-92-1 Y
ChEBI	CHEBI:28646 Y
ChemSpider	12063 Y
InChI InChI=1S/C3H5N5O/c4-1-6-2(5)8-3(9)7-1/h(H5,4,5,6,7,8,9) Y Key: MASBWURJQFFLOO-UHFFFAOYSA-N Y InChI=1/C3H5N5O/c4-1-6-2(5)8-3(9)7-1/h(H5,4,5,6,7,8,9) Key: MASBWURJQFFLOO-UHFFFAOYAL
Jmol-3D images	Image
KEGG	C08733 Y
PubChem	12583
SMILES O=C\1/N=C(/N)NC(=N/1)/N
Properties
Chemical formula	C3H5N5O
Molar mass	127.11 g/mol
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 noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

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

Synthesis

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

2C₂H₄N₄ + C₂H₅N₃O₂ → 2C₃H₅N₅O + NH₃

Chemical property

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, "Melamines and derivatives of melamine", Chemical Reviews, vol.58, p131-172 (1958).