2-(2-bromophenyl)-2-oxoacetic acid

2-(2-bromophenyl)-2-oxoacetic acid Property

Melting point:

104-107 °C

Boiling point:

330.5±34.0 °C(Predicted)

Density 

1.738±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

pka

1.91±0.54(Predicted)

Appearance

White to off-white Solid

Safety

HazardClass 

IRRITANT

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

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

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

2-(2-bromophenyl)-2-oxoacetic acid Chemical Properties,Usage,Production

Synthesis

A solution of 1-(2-bromophenyl)ethan-1-one (10 g, 50.24 mmol, 1.00 eq.) in pyridine (80 mL) was added to a 250 mL three-necked round-bottomed flask under nitrogen protection. Selenium dioxide (22 g, 198.27 mmol, 3.95 equiv) was then added. The reaction mixture was placed in a 120°C oil bath and stirred for 18 hours. After completion of the reaction, it was cooled to room temperature and filtered to remove solids. The filtrate was concentrated under reduced pressure and the residue was dissolved in 100 mL of water. The aqueous phase was washed with ethyl acetate (2×50 mL), and then the pH of the aqueous phase was adjusted to 1-2 with 4 mol/L hydrochloric acid.The aqueous phase was extracted with ethyl acetate (3×80 mL), and the organic phases were combined and dried with anhydrous sodium sulfate. The desiccant was removed by filtration and the filtrate was concentrated under reduced pressure to give 2-(2-bromophenyl)-2-oxoacetic acid (10 g, 87% yield) as a yellow oil. Mass spectrum (ESI) m/z 230 ([M + H]+).

References

[1] Patent: WO2017/168368, 2017, A1. Location in patent: Page/Page column 17
[2] Patent: WO2014/143960, 2014, A1. Location in patent: Page/Page column 33
[3] Tetrahedron, 2007, vol. 63, # 12, p. 2695 - 2711
[4] Chemical Communications, 2013, vol. 49, # 35, p. 3640 - 3642
[5] Advanced Synthesis and Catalysis, 2013, vol. 355, # 8, p. 1517 - 1522