Benzyl ether Property

Melting point:

1.5-3.5 °C(lit.)

Boiling point:

298 °C(lit.)

Density 

1.043 g/mL at 25 °C(lit.)

vapor pressure 

<1 Pa (25 °C)

FEMA 

2371 | DIBENZYL ETHER

refractive index 

n20/D 1.562

Flash point:

275 °F

storage temp. 

2-8°C

solubility 

42mg/l insoluble

form 

Liquid

color 

Clear colorless to pale yellow

Relative polarity

3.3

Odor

at 100.00 %. sweet fruity cherry earthy mushroom rose plastic

Odor Type

earthy

Water Solubility 

insoluble

JECFA Number

1256

Merck 

14,1132

BRN 

1911156

Dielectric constant

3.8599999999999999

Stability:

Stable. Combustible. Incompatible with strong acids, strong oxidizing agents.

LogP

3.31

CAS DataBase Reference

103-50-4(CAS DataBase Reference)

NIST Chemistry Reference

Benzene, 1,1'-[oxybis(methylene)]bis-(103-50-4)

EPA Substance Registry System

Benzyl ether (103-50-4)

Safety

Hazard Codes 

Xi,N

Risk Statements 

36/37/38-51/53

Safety Statements 

23-61

RIDADR 

UN 3082 9/PG 3

WGK Germany 

2

RTECS 

DQ6125000

F 

9

Autoignition Temperature

470 °C

TSCA 

Yes

HS Code 

2909 30 90

HazardClass 

9

PackingGroup 

III

Hazardous Substances Data

103-50-4(Hazardous Substances Data)

Toxicity

LD50 orally in Rabbit: 2500 mg/kg

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H317May cause an allergic skin reaction

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P272Contaminated work clothing should not be allowed out of the workplace.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P333+P313IF SKIN irritation or rash occurs: Get medical advice/attention.

Benzyl ether Chemical Properties,Usage,Production

Chemical Properties

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

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.

Uses

Plasticizer for nitrocellulose; solvent in perfumery.

Uses

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.

Uses

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.

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.

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.

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.]