ChemicalBook CAS DataBase List METHYLDIPHENYLPHOSPHINE

METHYLDIPHENYLPHOSPHINE synthesis

8synthesis methods

Product Name:METHYLDIPHENYLPHOSPHINE
CAS Number:1486-28-8
Molecular formula:C13H13P
Molecular Weight:200.22

The mainstream preparation method for methyldiphenylphosphine typically involves a nucleophilic substitution reaction between a Grignard reagent or an organolithium reagent and chlorodiphenylphosphine. The most common approach involves first preparing methylmagnesium bromide (CH?MgBr) via a Grignard reaction, which is then added dropwise to a solution of chlorodiphenylphosphine in an inert solvent such as diethyl ether or tetrahydrofuran. After the reaction is complete, post-processing steps such as hydrolysis and extraction are performed to remove the byproduct magnesium chloride and unreacted starting materials. Finally, purification is performed by vacuum distillation or recrystallization to obtain the target product, methyldiphenylphosphine.

917-64-6 Synthesis

917-64-6
148 suppliers
$45.00/10ml

1079-66-9
466 suppliers
$5.00/5g

1486-28-8
169 suppliers
$9.00/1g

Yield:1486-28-8 74%

Reaction Conditions:

in diethyl ether at -35;Inert atmosphere;

Steps:

A solution of CH3MgIin Et2O(20 mL) was added dropwiseat - 35 °C to a solution of chlorodipenylphosphane (29.8 g,135.06 mmol) in Et2O(100 mL) at - 35 °C under N2andthe mixture was stirred for overnight. After filtration, theorganic phase was washed with distilled water (3 × 10 mL),separated and dried with anhydrous Na2SO4.Methyldiphenylphosphine(20 g, 99.90 mmol) was obtained as a colorlessliquid by reduced pressure distillation in 74% yield. 1H NMR(400 MHz, CDCl3,298 K): δ 1.6 (d, 3H, CH3),7.3-7.7 (m,10H, Ph). 31P NMR (162 MHz, CDCl3,298 K): δ - 26.8 (s).A solution of n-BuLi (21.5 mL, 2.4 mol/L in n-hexane,51.6 mmol) in n-hexane (30 mL) was added dropwise to asolution of methyldiphenylphosphine (10 g, 49.95 mmol)and TMEDA (6.1 g, 25 mL) in n-hexane (15 mL) at below0 °C. The reaction mixture was then stirred for 60 h underN2at room temperature. The yellow precipitate was filteredoff and washed with n-hexane (3 × 20 mL) to give (diphenylphosphino)methyllithium-TMEDA (16 g, 49.6 mmol,99% yield).

References:

Wei, Wei;Yu, Buwei;Alam, Fakhre;Huang, Yongwang;Cheng, Shaoling;Jiang, Tao [Transition Metal Chemistry,2019,vol. 44,# 2,p. 125 - 133]

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