192461-80-6

Basic information

• Product Name: Phosphinic amide, N-(2,3-dihydro-1H-inden-1-ylidene)-P,P-diphenyl-, (E)-
• CAS NO: 192461-80-6
• Molecular Formula: C21H18NOP
• Molecular Weight: 331.354
• Mol File: 192461-80-6.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: Phosphinic amide, N-(2,3-dihydro-1H-inden-1-ylidene)-P,P-diphenyl-, (E)-(CAS DataBase Reference)
• NIST Chemistry Reference: Phosphinic amide, N-(2,3-dihydro-1H-inden-1-ylidene)-P,P-diphenyl-, (E)-(192461-80-6)
• EPA Substance Registry System: Phosphinic amide, N-(2,3-dihydro-1H-inden-1-ylidene)-P,P-diphenyl-, (E)-(192461-80-6)

Safety Data

• Hazardous Substances Data: 192461-80-6(Hazardous Substances Data)

Upstream product

• 68253-35-0 indan-1-one oxime 
• 1079-66-9 chloro-diphenylphosphine 
• 68253-35-0 (E)-indan-1-one oxime 
• 83-33-0 inden-1-one 
• 1499-21-4 Diphenylphosphinic chloride 

Downstream Products

• 10277-74-4 (S)-1-Aminoindane 
• 192461-85-1 (S)-(-)-N-(1-indanamine)diphenylphosphinamide 

Relevant articles and documents

Enantioselective Hydrogenation of Activated Aryl Imines Catalyzed by an Iron(II) P-NH-P′ Complex

Chiral amines are key building blocks in synthetic chemistry with numerous applications in the agricultural and pharmaceutical industries. Asymmetric imine hydrogenation, particularly with iridium catalysts, is well developed. However, imine reduction still remains challenging in the context of replacing such a precious metal with a cheap, nontoxic, and environmentally friendly substitute such as iron. Here, we report that an unsymmetrical iron P-NH-P′ catalyst that was previously shown to be effective for the asymmetric hydrogenation of aryl ketones is also a very effective catalyst for the asymmetric hydrogenation of prochiral aryl imines activated with N-diphenylphosphinoyl or N-tosyl groups. The P-NH-P′ abbreviation stands for (S,S)-PPh2CHPhCHPhNHCH2CH2PiPr2. Density functional theory results suggest that, surprisingly, the NH group on the catalyst activates and orients the imine to hydride attack by hydrogen bonding to the PO or SO group on the imine nitrogen, as opposed to the imine nitrogen itself. This may explain why N-Ph and N-Bu imines are not hydrogenated.

Zinc-catalyzed enantioselective hydrosilylation of imines

The highly enantioselective reduction of imines is achieved by employing chiral Zn/diamine catalysts. This new catalytic protocol offers attractive features such as use of a non-precious metal and an inexpensive silane, easy modification of chiral diamine

Enantioselective borohydride reduction catalyzed by optically active cobalt complexes

The highly enantioselective borohydride reduction of aromatic ketones or imines to the corresponding alcohols was developed in the presence of a catalytic amount of an optically active cobalt(II) complex catalyst. This enantioselective reduction is carried out using a precisely premodified borohydride with alcohols such as tetrahydrofurfuryl alcohol, ethanol and methanol. High optical yields are obtained by choosing the appropriate alcohol as modifiers and a suitable β-ketoiminato ligand of the catalyst. The enantioselective borohydride reduction has been successfully applied to the preparation of optically active 1,3-diols, the stereoselective reduction of diacylferrocenes, and dynamic and/or kinetic resolution of 1,3-dicarbonyl compounds.