22950-48-7

Basic information

• Product Name: 3-(diphenylphosphoryl)-1-phenylpropan-1-ol
• CAS NO: 22950-48-7
• Molecular Formula: C₂₁H₂₁O₂P
• Molecular Weight: 336.364
• Mol File: 22950-48-7.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 497.7°C at 760 mmHg
• Flash Point: 254.8°C
• Density: 1.18g/cm³
• Vapor Pressure: 1.01E-10mmHg at 25°C
• Refractive Index: 1.611
• CAS DataBase Reference: 3-(diphenylphosphoryl)-1-phenylpropan-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(diphenylphosphoryl)-1-phenylpropan-1-ol(22950-48-7)
• EPA Substance Registry System: 3-(diphenylphosphoryl)-1-phenylpropan-1-ol(22950-48-7)

Safety Data

• Hazardous Substances Data: 22950-48-7(Hazardous Substances Data)

Upstream product

• 96-09-3 styrene oxide 
• 2129-89-7 diphenyl(methyl)phosphine oxide 

Downstream Products

• 69803-60-7 (β-benzoylethyl)diphenylphosphine oxide 
• 101680-89-1 3-diphenylphosphinoyl-1-phenylpropyl cyclopropanecarboxylate 
• 345661-79-2 3-diphenylphosphinoyl-1-phenylbutan-1-ol 
• 176242-50-5 (S)-1-Phenyl-3-diphenylphosphinoylpropan-1-yl benzoate 
• 246253-23-6 3-Diphenylphosphinoyl-1-phenylpropyl benzyl ether 
• 89358-50-9 3-diphenylphosphinoyl-1-phenylbutan-1-one 
• 101680-92-6 2-diphenylphosphinoyl-1-cyclopropyl-4-hydroxy-4-phenylbutan-1-one 
• 105445-38-3 5-(Diphenyl-phosphinoyl)-7-hydroxy-4-oxo-7-phenyl-heptanoic acid methyl ester 
• 105445-37-2 7-(tert-Butyl-diphenyl-silanyloxy)-5-(diphenyl-phosphinoyl)-4-oxo-7-phenyl-heptanoic acid methyl ester 

Relevant articles and documents

The lithiation and acyl transfer reactions of phosphine oxides, sulfides and boranes in the synthesis of cyclopropanes

Phosphine oxides are lithiated much faster than phosphine sulfides and phosphine boranes. Phosphine sulfides are in turn lithiated much more readily than phosphine boranes. It was possible to trap a phosphine sulfide THF in one case which upon treatment with t-BuOK gave cyclopropane, showing that phosphine sulfides readily undergo both phosphinoyl transfer and cyclopropane ring closure just like their phosphine oxide counterparts. The obtained data show that phosphine oxides are easily lithiated and undergo phosphoryl transfer much more readily and faster than phosphine sulfides and phosphine boranes. The observations suggest that it would be possible to perform reactions involving phosphine oxides in the presence of phosphine boranes or phosphine sulfides, potentially allowing regioselective alkylation of phosphine oxides in the presence of phosphine boranes or phosphine sulfides.

ACYL TRANSFER REACTIONS WITH PHOSPHINE OXIDES: SYNTHESIS OF E-HOMOALLYLIC ALCOHOLS, CYCLOPROPYL KETONES, AND γ-HYDROXY KETONES

Esters of 3-hydroxypropylphosphine oxides rearrange in base by O to C acyl (RCO) transfer to give the hydroxy ketones (8). threo-Selective reduction of (8) leads to pure E-homoallylic alcohols whilst C to O acyl )Ph2PO) transfer leads to γ-hydroxy ketones with nucleophilic aqueous base or cyclopropyl ketones with BuOKt - HOBut.

Synthesis of β-(Diphenylphosphinoyl) Ketones

The title compounds may be made by addition of phosphorus nucleophiles (Ph2PO-, Ph2POMgX, Ph2PCl) to enones, by addition of phosphorus-stabilised carbanions to a α-carbonyl cation equivalents (2,3-dichloropropene, epoxides, and α-MeO-ketones) and by oxidation of allyl diphenylphosphine oxides.