DPPH

CAS 72804-96-7, Cat. No EN300-101508
Reagent for electrophilic amination and N-deletion in amines

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DPPH (O-diphenylphosphinyl hydroxylamine) is an electrophilic amination reagent that occupies a unique niche in organic synthesis. It is a solid, bench-stabile for a year compound with very low solubility in aprotic organic solvents¹. This reagent rapidly reacts with the NH group in imidazoles, xanthines, indoles, and carbazoles. The usage of DPPH is a reliable method for N-amination of many primary and secondary amines^2,3 that starts with deprotonation (e.g. with NaH) followed by further treatment with the reagent. Stabilized carbanions or Grignard reagents can serve as substrates for reaction as well^1,2. The newly developed methodology allows nitrogen deletion with the DPPH from secondary amines⁴. This reaction demonstrates high functional tolerance and can be applied to α-primary, α-secondary, and α-tertary alkylamines.

Synonyms: azanyl P,P-diphenylphosphinate (ACI); hydroxylamine, O-(diphenylphosphinyl)- (9CI); (aminooxy)diphenylphosphine oxide; O-(diphenylphosphoryl)hydroxylamine; O-diphenylphosphinylhydroxylamine