2-BROMODIPHENYL ETHER

2-BROMODIPHENYL ETHER Property

Melting point:

43.5-44.5 °C(Solv: methanol (67-56-1))

Boiling point:

97-100 °C(Press: 0.1 Torr)

Density 

1.413±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Chloroform (Slightly), DMSO (Slightly, Sonicated), Methanol (Slightly)

form 

Low-Melting Solid to Solid

color 

White to Off-White

EPA Substance Registry System

PBDE 001 (7025-06-1)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H312Harmful in contact with skin

H332Harmful if inhaled

Precautionary statements

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

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

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

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

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

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P322Specific measures (see …on this label).

P330Rinse mouth.

P363Wash contaminated clothing before reuse.

P501Dispose of contents/container to..…

2-BROMODIPHENYL ETHER Chemical Properties,Usage,Production

Uses

1-Bromo-2-phenoxybenzene can be used for quantification for trace polybrominated di-Ph ether in biota samples from electronic waste recycling area.

Synthesis

2-Bromophenol (0.211 mL, 2 mmol) and phenylboronic acid (490 mg, 4 mmol) were added with copper acetate (364 mg, 2 mmol), triethylamine (TEA, 1.38 mL, 10 mmol) and 4A molecular sieves in dichloromethane (DCM, 25 mL). The reaction mixture was stirred at room temperature for 18 hours. After completion of the reaction, the slurry was filtered through diatomaceous earth and the filtrate was concentrated under reduced pressure. The concentrate was diluted with ethyl acetate (EtOAc) and sodium bicarbonate (NaHCO3) solution for extraction. The organic phase was washed with brine and dried with anhydrous magnesium sulfate (MgSO4). The crude product was purified by fast column chromatography (eluent: hexane) to afford the target product 2-bromodiphenyl ether (232 mg, 47% yield) as a colorless oil. The product was detected by thin-layer chromatography (TLC) with an Rf value of 0.75 (unfolding agent: DCM); liquid chromatography-mass spectrometry (LCMS) analysis showed a retention time (U) of 1.3 min (mobile phase: 95% aqueous methanol), and mass-to-charge ratios (m/z) of 246.84 and 248.86 (MH+); high performance liquid chromatography (HPLC) analysis showed a retention time (U ) was 2.88 min (mobile phase: 90% aqueous acetonitrile) and the purity was 98%. Nuclear magnetic resonance hydrogen spectroscopy (1H NMR, CDCl3, 270 MHz) data: δ 6.95-7.04 (4H, m, ArH), 7.11 (1H, td, J = 1.1, 8.0 Hz, ArH), 7.22-7.37 (3H, m, ArH), 7.61-7.65 (1H, m, ArH). Nuclear magnetic resonance carbon spectroscopy (13C NMR, CDCl3, 68 MHz) data: 115.0 (ArC), 118.2, 120.7, 123.5, 125.1, 128.8, 129.9, 133.9 (ArCH), 153.8, 156.9 (ArC).

References

[1] Patent: WO2009/66072, 2009, A2. Location in patent: Page/Page column 99
[2] Patent: US2014/228568, 2014, A1. Location in patent: Paragraph 0162-0163
[3] Journal of Medicinal Chemistry, 2004, vol. 47, # 3, p. 744 - 755
[4] Patent: WO2014/100695, 2014, A1. Location in patent: Paragraph 00386