Bis(4-bromophenyl) ether Chemical Properties

Melting point:

61-63 °C(lit.)

Boiling point:

338-340 °C(lit.)

Density 

1.6728 (rough estimate)

refractive index 

1.6260 (estimate)

Flash point:

338-340°C

storage temp. 

2-8°C

solubility 

Methanol (Slightly)

form 

Crystalline

color 

White

Water Solubility 

Soluble in water.

InChI

InChI=1S/C12H8Br2O/c13-9-1-5-11(6-2-9)15-12-7-3-10(14)4-8-12/h1-8H

InChIKey

YAWIAFUBXXPJMQ-UHFFFAOYSA-N

SMILES

O(C1=CC=C(Br)C=C1)C1=CC=C(Br)C=C1

CAS DataBase Reference

2050-47-7(CAS DataBase Reference)

NIST Chemistry Reference

4-Bromophenyl ether(2050-47-7)

EPA Substance Registry System

p,p'-Dibromodiphenyl ether (2050-47-7)

Safety Information

Hazard Codes 

F,Xn,N

Risk Statements 

33-67-65-50/53-38-11

Safety Statements 

24/25-62-61-60-33-29-16-9

RIDADR 

UN 1262 3/PG 2

WGK Germany 

3

RTECS 

KN0175000

TSCA 

Yes

HS Code 

29093090

Toxicity

LD50 ipr-mus: 125 mg/kg NTIS** AD277-689

MSDS

• Language:English Provider:Bis(4-bromophenyl) ether
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
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Bis(4-bromophenyl) ether Usage And Synthesis

Chemical Properties

Tan or light crystalline

Uses

PBDE 15 is a polybrominated di-?Ph ether (PBDE), which is a flame retardant often incorporated into many polymers. PBDEs are an environmental pollutant that exhibit potential health risks to humans and wildlife.

Safety Profile

Poison by intraperitoneal route. When heated todecomposition it emits toxic fumes of Br-.

Synthesis

The general procedure for the synthesis of 4,4'-dibromodiphenyl ether from diphenyl ether was as follows: in a four-necked round-bottomed flask fitted with a stirrer, condenser, dropping funnel and thermometer, diphenyl ether (170 g, 1.0 mol), 1,2-dichloroethane (EDC) (300 ml), water (200 ml) and NaBrO3 (55 g, 0.36 mol) were added. Bromine (176 g, 1.1 mol) was slowly added dropwise to the stirred mixture for 1 h at 25 °C. No significant HBr gas was released during the reaction. The reaction progress was monitored by gas chromatography (GC). After two hours of reaction, the diphenyl ether was completely converted to 4,4'-dibromodiphenyl ether. The reaction was stopped and the phases were separated to give the crude product 4,4'-dibromodiphenyl ether (324.8 g) in 99% yield and 99.5% selectivity.

References

[1] Patent: EP429975, 1991, A1
[2] Angewandte Chemie - International Edition, 2018, vol. 57, # 20, p. 5938 - 5942
[3] Angew. Chem., 2018, vol. 130, p. 6044 - 6049,6
[4] Monatshefte fuer Chemie, 1992, vol. 123, # 12, p. 1153 - 1162
[5] Patent: EP429975, 1991, A1

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