3-PHENOXYBROMOBENZENE Chemical Properties

Boiling point:

200-203℃ (50 Torr)

Density 

1.3944 g/cm3 (20℃)

refractive index 

1.6076 (589.3 nm 20℃)

Flash point:

>110℃

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Sparingly), Ethyl Acetate (Slightly), Methanol (Sparingly)

form 

liquid

color 

Colourless

EPA Substance Registry System

PBDE 002 (6876-00-2)

Safety Information

Hazard Codes 

Xi,N

Risk Statements 

37/38-41-43-51/53

Safety Statements 

26-36/37/39-61

RIDADR 

UN 3077 9 / PGIII

WGK Germany 

3

RTECS 

CY9040554

Hazard Note 

Irritant

HS Code 

2909303890

3-PHENOXYBROMOBENZENE Usage And Synthesis

Uses

1-Bromo-3-phenoxybenzene is part of a group of compounds called polybrominated diphenyl ethers. 1-Bromo-3-phenoxybenzene, along with other similar compounds, are widely used in industry as brominated flame retardants. Unfortunately, with their release into the environment, they pose significant hazards to the humans and wildlife that live in surrounding areas. 1-Bromo-3-phenoxybenzene is also known to induce toxic effects on the central nervous system, the liver, and kidneys in rats.

Synthesis

Example 6 Synthesis of 1-bromo-3-phenoxybenzene (A): a mixture of meso-dibromobenzene (3 g, 12.75 mmol), phenol (1 g, 10.6 mmol), copper(I) oxide (152 mg, 1 mmol), and cesium carbonate (3.46 g, 10.6 mmol) was dissolved in 8 mL of N-methylpyrrolidone (NMP). The reaction mixture was microwaved at 195 °C for 20 min. Upon completion of the reaction, the non-homogeneous mixture was filtered through a bed of diatomaceous earth and the residue was washed with ethyl acetate (EtOAc, 1 × 20 mL). The filtrate was diluted with 1N sodium hydroxide solution (200 mL) and subsequently extracted with ethyl acetate (3 × 100 mL). The organic phases were combined, dried with anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure to give the crude product as a yellow oil. The crude product was purified by column chromatography (100% hexane as eluent) to afford 1-bromo-3-phenoxybenzene as a colorless oil (1.4 g, 53% yield).LCMS m/z 250 (M + 1).

References

[1] Patent: US2005/234042, 2005, A1. Location in patent: Page/Page column 25-26
[2] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 16, p. 5900 - 5905
[3] Patent: EP1489077, 2004, A1. Location in patent: Page 31

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