Di-n-butylmagnesium

Chemical Properties

The pure substance is a waxy solid. Commercially, it is marketed as solution inheptane. Di-n-butylmagnesium solution is a useful reagent for the synthesis of organomagnesium compounds.

Uses

Electrochemically inactive [Mg₂(μ-Cl)₃.6THF][C₂H₅AlCl₃] crystal may be obtained from an electrolyte composed of Di-n-butylmagnesium and ethylaluminum dichloride. Di-n-butylmagnesium may be used in the carbon metallation of α-olefins. A study reports the possible use of the organometallic compound in the intercalation of magnesium and zinc into the layers of TiS₂ or WO₂Cl₂. Interaction of lithium alkoxide with di-n-butylmagnesium was investigated.

Application

Di-n-butylmagnesium solution can be used as a reagent for the deprotection of aromatic and aliphatic benzyl thioethers to synthesize corresponding benzylthiols in the presence of titanocene dichloride. It can also be used as a catalyst to synthesize enantioenriched nitrogen-containing heterocyclic derivatives by the asymmetric ring-opening reaction of aziridines with substituted tetrazoles in the presence of chiral ligand.

General Description

Contains up to 1 wt. % Triethylaluminum as a viscosity reducer. stable under normal temperature and pressure, sensitive to light. contact with water releases flammable gas.

reaction suitability

reaction type: Grignard Reaction

Synthesis

1, the preparation of sec-butylmagnesium chloride

To the 250mL four-necked flask equipped with a stirrer, dropping funnel, thermometer, nitrogen introduction tube and reflux condenser (on the drying tube) through nitrogen, add a certain amount of magnesium powder with a small amount of iodine stirring, and slowly heating. When the iodine partially sublimated, add a small amount of 2-chlorobutane ether solution, the reaction triggered by the remaining 2-chlorobutane ether solution through the dropping funnel slowly dripping, dropping time of about 1h. After the reaction was completed, the reaction was left to stratify, and the upper layer of the clear liquid was taken as sec-butylmagnesium chloride, and the magnesium content was determined by titration method and the yield was calculated.

2, the preparation of dibutyl magnesium

To the 250mL four flasks equipped with stirrer, nitrogen introduction tube, thermometer and reflux condenser (on the drying tube), add the reaction generated by the above sec-butylmagnesium chloride clear liquid, open the stirring, rapid addition of n-butyllithium hexane solution, the addition of finished to continue to react for 20min or so, the reaction is complete, static stratification, take the upper layer of clear liquid with potentiometric titration. The upper layer of the clear liquid with potentiometric titration to analyze the content of chloride ions, calculate the yield of dibutyl magnesium.