2,2'-Dibromodiethyl ether Chemical Properties

Boiling point:

92-93 °C12 mm Hg(lit.)

Density 

1.845 g/mL at 25 °C(lit.)

refractive index 

1.513

Flash point:

185 °F

storage temp. 

2-8°C

solubility 

Chloroform (Soluble), Methanol (Slightly)

form 

clear liquid

color 

Colorless to Light yellow to Light orange

Specific Gravity

1.845

Water Solubility 

Not miscible or difficult to mix with water.

BRN 

1098335

Stability:

This product may also contain 2-chloroethyl ether (CAS 111-44-4) or N,N-dimethylformamide (CAS 68-12-2) MSDS data for these materials should be consulted before use. Combustible. Incompatible with oxidizing agents, acid chlorides, chloroformates, reducing agents, halogens.

CAS DataBase Reference

5414-19-7(CAS DataBase Reference)

NIST Chemistry Reference

1-Bromo-2-(2-bromoethoxy)ethane(5414-19-7)

EPA Substance Registry System

Ethane, 1,1'-oxybis[2-bromo- (5414-19-7)

Safety Information

Hazard Codes 

T,Xi

Risk Statements 

61-37/38-41

Safety Statements 

53-26-36/37/39-45

RIDADR 

2810

WGK Germany 

3

TSCA 

Y

HazardClass 

6.1

PackingGroup 

III

HS Code 

29091990

MSDS

• Language:English Provider:2,2'-Dibromodiethyl ether
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2,2'-Dibromodiethyl ether Usage And Synthesis

Uses

2,2'-dibromodiethyl ether is an important organic intermediate (building block) to synthetize substituted diethyl ether products.

Description

Bis(2-bromoethyl) ether is an either compound with two terminal bromine atoms. Bis(2-bromoethyl) ether can be used as a building block for variety of pharmaceutical compounds and mateials.

Chemical Properties

colourless liquid

Uses

2-Bromoethyl ether (2,2′-Dibromodiethyl ether) may be used in the preparation of 1,4,7-trioxa-10-19-dithia-13,16-diaza-12,17-dioxo-8,9,14,15,20,21-tribenzoheneicosane.

General Description

2-Bromoethyl ether (2,2′-Dibromodiethyl ether) is a halogen containing ether. 2,2′-Dibromodiethyl ether has been prepared by reacting dioxane with anhydrous, bromine free hydrogen bromide.

Synthesis

General procedure for the synthesis of 2,2'-dibromodiethyl ether from diethylene glycol: 21.2 g (0.2 mol) of diethylene glycol was added to a dry 1 L three-necked flask, followed by the addition of 500 mL of carbon tetrachloride as a solvent, and a magnetic stirrer was turned on to dissolve the ingredients completely. The reaction system was cooled in an ice-water bath to 0 °C. Under stirring conditions, 60 g (0.22 mol) of phosphorus tribromide was slowly added dropwise using a constant-pressure dropping funnel, with the rate of dropwise acceleration being controlled to avoid intense exotherm. After the dropwise addition, the reaction was continued in an ice-water bath with stirring for 1 hour. Subsequently, the ice-water bath was withdrawn and the reaction mixture was allowed to warm up naturally to room temperature with continuous stirring for 15 h to ensure complete reaction. Upon completion of the reaction, the carbon tetrachloride solvent was removed by concentration under reduced pressure by rotary evaporator. To the residue, 500 mL of ethyl acetate was added for dissolution, followed by four washes with 5% aqueous sodium carbonate to neutralize the residual acid. The organic layer was separated and dried with anhydrous sodium sulfate. Finally, the ethyl acetate was removed by distillation under reduced pressure to give 41.4 g of the target product 2,2'-dibromodiethyl ether as a colorless oil.

IC 50

Alkyl-Chain

References

[1] Journal of Materials Chemistry B, 2014, vol. 2, # 29, p. 4640 - 4652
[2] Journal of Materials Chemistry B, 2015, vol. 3, # 8, p. 1495 - 1506
[3] Journal of Organic Chemistry, 1983, vol. 48, # 20, p. 3412 - 3422
[4] Journal of the American Chemical Society, 1937, vol. 59, p. 213
[5] Justus Liebigs Annalen der Chemie, 1937, vol. 528, p. 150

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