BIS(1,2-DIPHENYLARSENO)METHANE synthesis

8synthesis methods

Product Name:BIS(1,2-DIPHENYLARSENO)METHANE
CAS Number:21892-63-7
Molecular formula:C25H22As2
Molecular Weight:472.29

75-09-2 Synthesis

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Yield:21892-63-7 54%

Reaction Conditions:

Stage #1: hexaphenylcyclohexaarsane;phenyllithium in tetrahydrofuran at 0 - 20; for 2 h;Inert atmosphere;
Stage #2: dichloromethane in tetrahydrofuran at 0 - 20; for 19 h;Inert atmosphere;

Steps:

Bis(diphenylarsino)methane (dpam)

A THF dispersion (20 mL) of Ph₆As₆ (787 mg, 0.863 mmol) was cooled to 0 °C under N₂ atmosphere, and PhLi (1.6 M in butyl ether, 3.3 mL, 5.2 mmol) was slowly added. The reaction mixture was warmed to room temperature, and stirred for 2 h. Again, the reaction mixture was cooled to 0 °C, and CH₂Cl₂ (160 mL, 2.6 mmol) was slowly added. After stirring at room temperature for 19 h, the reaction was quenched by distilled water. The resultant solution was extracted with CHCl₃ three times, and the combined organic layers were dried over MgSO₄. After filtration, the volatiles were removed in vacuo. The residue was subjected to recrystallization from CH₂Cl₂ and MeOH to obtain colorless crystals of dpam (661 mg, 1.40 mmol, 54%). ¹H NMR (CDCl₃, 400 MHz) δ 7.43-7.40 (m, 8H), 7.30-7.27 (m, 12H), 2.60 (s, 2H) ppm. This ¹H-NMR spectrum corresponds precisely to that of the previous literature.^[10] HRMS (FAB) m/z: calcd for C₂₅H₂₂As₂ [M]⁺: 472.0153, found 472.0165.

References:

Imoto, Hiroaki;Konishi, Masafumi;Nishiyama, Shintaro;Sasaki, Hiroshi;Tanaka, Susumu;Yumura, Takashi;Naka, Kensuke [Chemistry Letters,2019,vol. 48,# 11,p. 1312 - 1315] Location in patent:supporting information

75-09-2 Synthesis

75-09-2
1202 suppliers
$10.00/25ML