Cupferron

Cupferron
Cupferron
Identifiers
CAS number 135-20-6
PubChem 2724103
ChemSpider 2006262 YesY
Jmol-3D images Image 1
Properties
Molecular formula C6H9N3O2
Molar mass 155.15 g/mol
Density  ? g/cm3, ?
Melting point

150-155 °C

Solubility in water soluble
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Cupferron, the ammonium salt of N-nitroso-N-phenylhydroxylamine, is a common reagent for the complexation of metal ions. Its formula is NH4[C6H5N(O)NO]. The anion binds to metal cations through the two oxygen atoms, forming five-membered chelate rings.

Cupferron is prepared from phenylhydroxylamine and an NO+ source:

C6H5NHOH + C4H9ONO + NH3 → NH4[C6H5N(O)NO] + C4H9OH

References

  • C. S. Marvel “Cupferron” Organic Syntheses, Coll. Vol. 1, p.177; Vol. 4, p.19.
  • D. Van der Helm, L. L. Merritt Jnr, R. Degeilh and C. H. MacGillavry “The crystal structure of iron cupferron Fe(O2N2C6H5)3” Acta Cryst. (1965). 18, 355-362
  • Merck 13,2649; Beil. 16,IV,891