2-Bromo-5-trifluoromethylphenol Chemical Properties

Melting point:

22-23°

Boiling point:

56.0-57.5 °C(Press: 3.5-4.0 Torr)

Density 

1.752

storage temp. 

Inert atmosphere,Room Temperature

form 

Liquid

pka

7.43±0.10(Predicted)

color 

Pale brown

Safety Information

RIDADR 

UN1760

HazardClass 

IRRITANT

HazardClass 

8

HS Code 

2905599890

2-Bromo-5-trifluoromethylphenol Usage And Synthesis

Chemical Properties

light brown liquid

Uses

2-Bromo-3-(trifluoromethyl)phenol is used as a reactant in the synthesis of benzimidazolone and benzothiazolone compounds as AMPA receptor modulators.

Synthesis

General procedure for the synthesis of 2-bromo-5-trifluoromethylphenol from 3-trifluoromethylphenol: To a stirred solution of 61.65 g (0.38 mol) of 3-trifluoromethylphenol dissolved in 240 ml of carbon disulfide, 19.6 ml (0.38 mol) of bromine was slowly added dropwise. The reaction mixture was stirred continuously at room temperature for about 18 hours. Subsequently, the reaction solution was partitioned between 200 ml of dichloromethane and 100 ml of water. The organic phase was separated, washed with 20 mL of saturated aqueous sodium chloride, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography using dichloromethane containing 40% hexane as eluent. The eluate containing the target product was collected and concentrated under reduced pressure to give 48.8 g (53% yield) of 2-bromo-5-trifluoromethylphenol as a yellow oil. Ion spray mass spectrometry (MS) analysis showed m/e = 239,241 (M + 1).

References

[1] Journal of the American Chemical Society, 1951, vol. 73, p. 1325
[2] Journal of Organic Chemistry, 1951, vol. 16, p. 586,606
[3] Patent: US6638936, 2003, B1

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