Ammeline

Ammeline

Structural formula Ball-and-stick model
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 Number	645-92-1 Y
ChEBI	CHEBI:28646 Y
ChemSpider	12063 Y
Jmol 3D model	Interactive image
KEGG	C08733 Y
PubChem	12583
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
SMILES O=C\1/N=C(/N)NC(=N/1)/N
Properties
Chemical formula	C3H5N5O
Molar mass	127.11 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
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

Ammeline (4,6-diamino-2-hydroxy-1,3,5-triazine) is a triazine derivative. 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 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.