3-Bromo-5-chlorophenol Chemical Properties

Melting point:

66-70℃

Boiling point:

256°C (rough estimate)

Density 

1.6027 (rough estimate)

vapor pressure 

0.004-0.084Pa at 20-50℃

refractive index 

1.5730 (estimate)

storage temp. 

Inert atmosphere,2-8°C

pka

8.04±0.10(Predicted)

form 

Solid

Appearance

White to off-white Solid

LogP

3.2 at 25℃ and pH2

Surface tension

54.7mN/m at 1g/L and 20℃

CAS DataBase Reference

56962-04-0

Safety Information

HS Code 

2908190090

3-Bromo-5-chlorophenol Usage And Synthesis

Uses

3-Chloro-5-bromophenol is an important pharmaceutical intermediate that can be used in the preparation of a variety of pharmaceutical products.

Synthesis

General procedure for the synthesis of 3-bromo-5-chlorophenol from m-chlorobromobenzene: In an argon-purged flask, (1,5-cyclooctadiene)(methoxy)iridium(I) dimer (84 mg, 0.13 mmol), 4,4'-di-tert-butyl-2,2'-bipyridine (69 mg, 0.26 mmol), and bis(pinacolate)diboron (1.29 g, 5.11 mmol) were added. 5.11 mmol), followed by hexane (26 mL) and 1-bromo-3-chlorobenzene (1 mL, 8.51 mmol) sequentially. The reaction mixture was stirred at room temperature for 18 hours. Upon completion of the reaction, the mixture was concentrated under vacuum and redissolved in acetone (26 mL) followed by addition of an aqueous (26 mL) solution of Oxone (5.23 g, 8.51 mmol) [Note: exothermic phenomena were observed during the reaction].After 10 min, the reaction mixture was diluted with dichloromethane. The organic and aqueous layers were separated and the aqueous layer was extracted with dichloromethane. The organic phases were combined, washed with brine, dried and concentrated in vacuum to give 3-bromo-5-chlorophenol (1.43 g, 81% yield).LCMS (Method 3): retention time 3.74 min, mass-to-charge ratio m/z 205,207 [M-H+].

References

[1] Patent: US2014/364412, 2014, A1. Location in patent: Paragraph 0683; 0684
[2] Patent: WO2014/195402, 2014, A1. Location in patent: Page/Page column 217
[3] Patent: WO2009/115515, 2009, A1. Location in patent: Page/Page column 44-45
[4] Journal of the American Chemical Society, 2003, vol. 125, # 26, p. 7792 - 7793
[5] Synthesis, 2011, # 6, p. 857 - 859

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