Cupferron

Cupferron

Names
Other names cupferron ammonium N-nitrosophenylhydroxylamine
Identifiers
CAS Number	135-20-6
ChemSpider	2006262
Jmol interactive 3D	Image
PubChem	2724103
InChI InChI=1S/C6H5N2O2.H3N/c9-7-8(10)6-4-2-1-3-5-6;/h1-5H;1H3/q-1;/p+1 Key: GDEBSAWXIHEMNF-UHFFFAOYSA-O InChI=1/C6H5N2O2.H3N/c9-7-8(10)6-4-2-1-3-5-6;/h1-5H;1H3/q-1;/p+1 Key: GDEBSAWXIHEMNF-IKLDFBCSAP
SMILES O=NN([O-])c1ccccc1.[NH4+]
Properties
Chemical formula	C6H9N3O2
Molar mass	155.15 g/mol
Melting point	150 to 155 °C (302 to 311 °F; 423 to 428 K)
Solubility in water	soluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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 Crystallogr. (1965). 18, 355–362
• Merck 13,2649; Beil. 16,IV,891