Benzyl ether

Chemical properties

Dibenzyl ether is a clear, almost colorless liquid. It is miscible with alcohols and ethers, but insoluble in water. Dibenzyl ether is used as special solvent and delustering agent for textiles.

Chemical properties

Dibenzyl ether has a slightly earthy, mushroom-like odor with a rosy undertone.

The Uses of Benzyl ether

Benzyl ether is used as an effective GFP friendly tissue clearing medium for mouse brains. It is also used in a study to develop a detailed protocol for performing 3D imaging of solvent-cleared organs and its application to various microscopy techniques. It is also employed as a plasticizer for nitrocellulose and synthetic rubber, a solvent in perfumery, and a flavoring agent in chewing gums and baked goods.

The Uses of Benzyl ether

Plasticizer for nitrocellulose; solvent in perfumery.

The Uses of Benzyl ether

Benzyl ether was used as an effective GFP friendly tissue clearing medium for mouse brains. It was used in a study to develop a detailed protocol for performing 3D imaging of solvent-cleared organs and its application to various microscopy techniques.

Definition

ChEBI: Dibenzyl ether is a benzyl ether in which the oxygen atom is connected to two benzyl groups. It has a role as a metabolite.

Preparation

As a by-product in the preparation of benzyl alcohol by hydrolysis of benzyl chloride; by using a concentrated caustic instead of carbonate, yields can be improved to 50% or higher.

General Description

Colorless liquid with a mild odor.

Air & Water Reactions

Oxidizes readily in air to form unstable peroxides that may explode spontaneously [Bretherick, 1979 p.151-154, 164]. Insoluble in water.

Reactivity Profile

Benzyl ether can act as a base to form salts with strong acids and addition complexes with Lewis acids. May react violently with strong oxidizing agents. Burns readily but relatively inert in other reactions, which typically involve the breaking of the carbon-oxygen bond.

Hazard

Moderately toxic by ingestion. A skin irri- tant.

Health Hazard

Inhalation may cause nausea because of disagreeable odor. Contact of liquid with eyes causes mild irritation. Prolonged exposure of skin to liquid causes reddening and irritation. Ingestion produces nausea.

Fire Hazard

Benzyl ether is combustible.

Synthesis

Benzyl ether is formed when benzyl alcohol is heated with strong acids or bases. It is produced almost exclusively by the alkaline hydrolysis of benzyl chloride. Heat treatment decomposes dibenzyl ether into benzaldehyde and toluene.

Purification Methods

Reflux the ether over sodium, then distil it under reduced pressure. It been purified by fractional freezing. [Beilstein 6 IV 2240.]