ChemicalBook CAS DataBase List 1,3-Bis(diphenylphosphino)propane

1,3-Bis(diphenylphosphino)propane synthesis

9synthesis methods

Product Name:1,3-Bis(diphenylphosphino)propane
CAS Number:6737-42-4
Molecular formula:C27H26P2
Molecular Weight:412.45

3-(diphenylphosphoryl)propyl(diphenyl)phosphine oxide

16524-41-7

6737-42-4

GENERAL METHODS: In a sealed tube, the phosphine oxide derivative (5 mmol) was dissolved in anhydrous toluene (1 M), followed by the addition of InBr3 (1 mol%, 0.05 mmol) and TMDS (1.5 equiv, 7.5 mmol). Depending on the substrate, the reaction mixture was stirred at 100 °C for 7 to 40 h (the progress of the reaction was monitored by 31P NMR). Once the reaction was complete, toluene was removed by evaporation and the product was purified by rapid chromatography on silica gel, using pure cyclohexane as eluent, to give the final target product 1,3-bis(diphenylphosphino)propane.

16524-41-7
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6737-42-4
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Yield:6737-42-4 80%

Reaction Conditions:

with indium(III) bromide;1,1,3,3-Tetramethyldisiloxane in toluene at 100; for 22 h;Inert atmosphere;Sealed tube;

Steps:

General procedure for the preparation of compounds 2a, 2g and 2h.
General procedure: In a sealed tube containing a solution of the phosphine oxide derivative (5 mmol) in anhydrous toluene (1M) was added InBr₃ (1 mol %, 0.05 mmol) and the TMDS (1.5 equiv., 7.5 mmol). The reactionnal mixture was stirred at 100 °C during 7 to 40 h depending on the substrate (the reaction was monitored by ³¹P NMR). After complete consumption and evaporation of toluene the phosphine was purified by flash chromatography on silica gel with pure cyclohexane) to afford the desired phosphine.

References:

Pehlivan, Leyla;Métay, Estelle;Delbrayelle, Dominique;Mignani, Gérard;Lemaire, Marc [Tetrahedron,2012,vol. 68,# 15,p. 3151 - 3155] Location in patent:supporting information; experimental part

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109-64-8 Synthesis