DPPH

CAS 72804-96-7, Cat. No EN300-101508

Reagent for electrophilic aminations

DPPH is an electrophilic aminations reagent, that unique niche in organic synthesis. The reagent is a solid that has very low solubility in aprotic organic solvents and is bench-stable for a year^[1]. It rapidly reacts with the NH group of imidazoles and xanthines, indole, and carbazole. In fact, this reagent is a reliable way for N-amination of many secondary amines, or primary^{[2], [3]}. Usually, the procedure of N-amination with DPPH includes deprotonation (for example, with NaH) as the first step and as the second step treatment with reagent. Not only amino groups can be aminated with this reagent but also stabilized carbanions or Grignard reagents can be substrates for reaction^{[1], [2]}.

Synonyms: Azanyl P,P-diphenylphosphinate (ACI); Hydroxylamine, O-(diphenylphosphinyl)- (9CI); (Aminooxy)diphenylphosphine oxide; O-(Diphenylphosphoryl)hydroxylamine; O-Diphenylphosphinylhydroxylamine

Selected publication

1. O-(Diphenylphosphinyl)Hydroxylamine.

Boche G.; Belani J. D. Encyclopedia of Reagents for Organic Synthesis 2009. DOI: 10.1002/047084289X.rd432.pub2

2. (Diphenylphosphinyl)Hydroxylamine: A New Reagent for Electrophilic-Amination.

Colvin E. W.; Kirby G. W.; Wilson A. C. Tetrahedron Lett 1982, 23 (37), 3835–3836. DOI: 10.1016/S0040-4039(00)87720-5

3. Scalable Preparation of O-(Diphenylphosphinyl) Hydroxylamine (DPPH).

Tamas T. Organic Syntheses 2020, 97, 54–65. DOI: 10.15227/orgsyn.097.0054