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 Number	645-92-1
3D model (JSmol)	Interactive image
ChemSpider	12063 Y
ECHA InfoCard	100.010.415
KEGG	C08733
PubChem CID	12583
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) 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
Appearance	White powder
Melting point	N/A
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). Y verify (what is YN ?) 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 amond 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).