2-Bromo-5-chlorophenol Chemical Properties

Boiling point:

222.2±20.0 °C(Predicted)

Density 

1.788±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

form 

solid

pka

7.47±0.10(Predicted)

color 

White to off-white

Safety Information

Hazard Codes 

Xi

HS Code 

2908190090

2-Bromo-5-chlorophenol Usage And Synthesis

Chemical Properties

Pale yellow crystalline powder

Chemical Reactivity

The chemical reactions of 2-Bromo-5-chlorophenol include reactions with aminopyridine, isopropyl alcohol, chloroaniline, halophenols, dimethylamine, ethanolamine and toluidine. 2-Bromo-5-chlorophenol has been used as a reagent for the preparation of diethyl ethers and nitrates. This product has been used as a reagent for the synthesis of methyl groups and emulsifying agents for oil and water mixtures.

Synthesis

The general procedure for the synthesis of 2-bromo-5-chlorophenol using 3-chlorophenol as starting material was as follows: 5.03 g (39.1 mmol) of 3-chlorophenol was dissolved in 20 mL of dichloromethane, and the solution was cooled under ice bath conditions. Subsequently, 6.25 g (39.1 mmol) of bromine was added slowly and dropwise. The reaction mixture was gradually warmed to room temperature and stirred continuously for 16 hours. After completion of the reaction, the reaction mixture was diluted with water and phase separation was carried out. The organic phase was dried with magnesium sulfate. The residue was purified by silica gel column chromatography with an eluent ratio of 3:2 dichloromethane to hexane solvent mixture. The elution grade containing the target product 2-bromo-5-chlorophenol was collected and concentrated under reduced pressure to give 2.04 g (25% yield) of the pure product. High-resolution mass spectrometry (HRMS) results: calculated value of C6H4OClBr (M+) was 205.9134; measured value was 205.9125. Elemental analysis (EA) results: calculated value of C, 34.74; H, 1.94; measured value of C, 34.74; H, 1.76.

References

[1] Patent: EP1204659, 2003, B1. Location in patent: Page/Page column 30

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