Cupferron

Cupferron
Names
	Other names cupferron; ammonium N-nitrosophenylhydroxylamine
Identifiers
CAS Number	135-20-6;
ECHA InfoCard	100.004.713
CompTox Dashboard (EPA)	DTXSID1020352 ;
Properties
Chemical formula	C6H9N3O2
Molar mass	155.15 g/mol
Density	? g/cm3, ?
Melting point	150-155 °C
Solubility in water	soluble
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 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

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