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Wikipedia

Ammeline

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

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
  • 645-92-1 Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:28646 Y
ChemSpider
  • 12063 Y
ECHA InfoCard 100.010.415
KEGG
  • C08733 Y
  • 12583
UNII
  • LC8G9556Q0 Y
  • DTXSID3060950
  • 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
  • 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).
Y verify (what is YN ?)

Synthesis edit

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 edit

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 edit

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

ammeline, diamino, hydroxy, triazine, triazine, derivative, hydrolysis, product, melamine, structural, formula, ball, stick, modelnamespreferred, iupac, name, diamino, triazin, olother, names, diamino, hydroxy, triazine4, diamino, hydroxy, triazine4, diamino, . Ammeline 4 6 diamino 2 hydroxy 1 3 5 triazine is a triazine derivative It is the hydrolysis product of melamine 1 Ammeline Structural formula Ball and stick modelNamesPreferred IUPAC name 4 6 Diamino 1 3 5 triazin 2 olOther names 2 4 Diamino 6 hydroxy 1 3 5 triazine4 6 Diamino 2 hydroxy 1 3 5 triazine4 6 diamino 1 3 5 triazin 2 1H oneIdentifiersCAS Number 645 92 1 Y3D model JSmol Interactive imageChEBI CHEBI 28646 YChemSpider 12063 YECHA InfoCard 100 010 415KEGG C08733 YPubChem CID 12583UNII LC8G9556Q0 YCompTox Dashboard EPA DTXSID3060950InChI InChI 1S C3H5N5O c4 1 6 2 5 8 3 9 7 1 h H5 4 5 6 7 8 9 YKey MASBWURJQFFLOO UHFFFAOYSA N YInChI 1 C3H5N5O c4 1 6 2 5 8 3 9 7 1 h H5 4 5 6 7 8 9 Key MASBWURJQFFLOO UHFFFAOYALSMILES O C 1 N C N NC N 1 NPropertiesChemical formula C 3H 5N 5OMolar mass 127 107 g mol 1Appearance White powderMelting point N A decomposes before melting Solubility in water TraceSolubility Soluble in aqueous alkalies and mineral acids but not acetic acidExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox referencesSynthesis editAmmeline 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 NH3Chemical properties editAmmeline 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 edit B Bann and S A Miller 1958 Melamines and derivatives of melamine Chemical Reviews 58 131 172 doi 10 1021 cr50019a004 Retrieved from https en wikipedia org w index php title Ammeline amp oldid 1193767903, wikipedia, wiki, book, books, library,

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