| Identification | Back Directory | [Name]
O-DIPHENYLPHOSPHINYLHYDROXYLAMINE | [CAS]
72804-96-7 | [Synonyms]
O-DiphenyL
phosphinyL
diphenylphosphinate
aMino diphenylphosphinate
(AMinooxy)diphenylphosphineoxid
TwoPhenylphosphonichydroxylaMine
Diphenylphosphonoyl hydroxylamine
(AMinooxy)diphenylphosphine oxide
O-DIPHENYLPHOSPHINYLHYDROXYLAMINE
O-(diphenylphosphoryl)hydroxylaMine
HydroxylaMine, O-(diphenylphosphinyl)-
O-(Diphenylphosphinyl)hydroxylamine
Phosphinic acid, P,P-diphenyl-, azanyl ester | [Molecular Formula]
C12H14NO2P | [MDL Number]
MFCD03788194 | [MOL File]
72804-96-7.mol | [Molecular Weight]
235.22 |
| Chemical Properties | Back Directory | [Melting point ]
>140℃ (decomposition) | [Boiling point ]
368.0±25.0 °C(Predicted) | [density ]
1.25±0.1 g/cm3(Predicted) | [storage temp. ]
2-8°C | [solubility ]
DMSO (Slightly), Methanol (Very Slightly, Sonicated) | [form ]
solid | [pka]
-1.65±0.70(Predicted) | [color ]
white | [InChI]
InChI=1S/C12H12NO2P/c13-15-16(14,11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H,13H2 | [InChIKey]
SJECIYLGISUNRO-UHFFFAOYSA-N | [SMILES]
P(C1=CC=CC=C1)(C1=CC=CC=C1)(ON)=O |
| Hazard Information | Back Directory | [Chemical Properties]
Light yellow or white powder solid | [Uses]
Efficient reagent for direct conversion of aldehydes to nitriles in the presence of alcohol, ketone, ester, or amine functionality. | [Synthesis Reference(s)]
Tetrahedron Letters, 23, p. 3835, 1982 DOI: 10.1016/S0040-4039(00)87720-5 | [Description]
O-Diphenylphosphinylhydroxylamine (DPPH) is a versatile electrophilic amination reagent that has been used widely for the amination of stable carbanions, Grignard reagents, and π-electron-rich nitrogen heterocycles. Researchers have used DPPH for the aziridination of enones. Compared to other hydroxylamine derivatives typically stored as hydrochloride salts, this activated phosphinyl reagent exhibits good stability and can be stored indefinitely at 0 ℃. This compound in a single step from hydroxylamine hydrochloride and diphenylphosphinic chloride[1]. | [General Description]
O-(Diphenylphosphinyl)hydroxylamine is a general reagent for electrophilic C-amination, which aminates a variety of stable carbanions and Grignard reagents. | [References]
[1] J. P. Anselm, J. L. Ferrari. “A New Journal for Organic Synthesis: Organic Preparations and Procedures International.” Journal of Chemical Education 48 5 (1971): 349.
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