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ChemicalBook CAS DataBase List Dibenzyl diselenide
1482-82-2

Dibenzyl diselenide synthesis

13synthesis methods
Dibenzyl diselenide was synthesized from bis(methoxymagnesium) diselenide reagent as reported by Gunther using benzyl chloride (6.3 g, 0.05 mole) and a methanolic solution of bis(methoxymagnesium) diselenide reagent (from 0.05 gatom of selenium). After 10 min stirring, water (100 mL) and concentrated hydrochloric acid (5 mL) were added, the solution was cooled, and the black solid was collected by filtration. This black solid was then extracted with ethanol to yield a bright yellow solution which, upon solvent removal, gave a yellow crystalline product. The 1H NMR of the yellow solid (in CDCl3) was identical to that of commercially available dibenzyl diselenide.
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Yield:1482-82-2 97%

Reaction Conditions:

with selenium;potassium hydroxide in water at 60; for 0.5 h;Green chemistry;

Steps:

Symmetrical dialkyl disulfides and dialkyl diselenides synthesis; General Procedure

General procedure: RX (2.0 mmol), S (0.064 g, 2.0 mmol) and KOH (0.224 g,4 mmol) were added a flask containing H2O (0.5 mL). The reaction mixture was stirred at 60°C under atmospheric conditions until completion (30 min). Upon completion of the reaction, the mixture was extracted with CH2Cl2 (3 × 5 mL) and the combined organic phase was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. After, the residue was purified by plate chromatography to afford the corresponding product. Diselenides were synthesized analogously starting from selenium powder.

References:

Soleiman-Beigi, Mohammad;Yavari, Issa;Sadeghizadeh, Fatemeh [Phosphorus, Sulfur and Silicon and the Related Elements,2018,vol. 193,# 1,p. 41 - 44]

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