2-BROMO-5-METHOXYPHENYLBORONIC ACID Chemical Properties

Melting point:

214-216

Boiling point:

376.6±52.0 °C(Predicted)

Density 

1.61±0.1 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

solid

pka

7.82±0.58(Predicted)

color 

Beige

Safety Information

Hazard Codes 

Xi

Hazard Note 

Irritant

HS Code 

2931900090

2-BROMO-5-METHOXYPHENYLBORONIC ACID Usage And Synthesis

Synthesis

Under argon protection, 3-methoxyphenylboronic acid (9.12 g, 60.0 mmol) was dissolved in dichloromethane (200 mL) with triphenylphosphine sulfide (932 mg, 6.00 mmol) in a 300 mL aubergine flask, and stirred until completely dissolved. Subsequently, N-bromosuccinimide (13.0 g, 72.0 mmol) was added to the solution and stirred continuously for 48 hours at room temperature. Upon completion of the reaction, saturated aqueous sodium thiosulfate solution was added to quench the reaction. Extraction was carried out with dichloromethane (100 mL × 3) and the organic phases were combined, washed with saturated brine and dried over anhydrous sodium sulfate. After filtration, the crude product was concentrated under reduced pressure. The target product 2-bromo-5-methoxyphenylboronic acid (8.45 g, 36.6 mmol, 61.0% yield) was purified by silica gel column chromatography (silica gel 290 g, eluent hexane/acetone = 1/1).

References

[1] Organic Letters, 2010, vol. 12, # 11, p. 2480 - 2483
[2] Patent: JP2018/30788, 2018, A. Location in patent: Paragraph 0057
[3] Organic Letters, 2015, vol. 17, # 4, p. 1042 - 1045

2-BROMO-5-METHOXYPHENYLBORONIC ACID(89694-44-0)Related Product Information

• 3-Bromo-5-methoxybenzeneboronic acid
• 5-BROMO-2-METHOXYPHENYLBORONIC ACID
• 2-BROMO-5-METHOXYPHENYLBORONIC ACID
• (2,6-DIBROMO-5-METHOXY)BENZENEBORONIC ACID
• 6-Bromo-3-ethoxy-2-fluorobenzeneboronic acid
• 3-Benzyloxy-6-bromo-2-chlorophenylboronic acid
• 3-(Benzyloxy)-6-bromo-2-fluorophenylboronic acid
• 6-Bromo-2-fluoro-3-methoxybenzeneboronic acid
• (2,4-DIBROMO-5-METHOXY)BENZENEBORONIC ACID
• 6-Bromo-2-chloro-3-ethoxyphenylboronic acid
• 2-Bromo-5-(trifluoromethoxy)phenylboronic acid
• 6-Bromo-2-chloro-3-methoxyphenylboronic acid
• 6-BROMO-2-FLUORO-3-PROPOXYPHENYLBORONIC ACID
• 2-(6-BROMO-2-FLUORO-3-METHOXYPHENYL)-1,3,2-DIOXABOROLANE
• 6-BROMO-2-FLUORO-3-ISOPROPOXYPHENYLBORONIC ACID
• 6-BROMO-3-BUTOXY-2-FLUOROPHENYLBORONIC ACID
• 3-BROMO-2-METHOXYPHENYLBORONIC ACID
• 3-BROMO-5-METHOXYPHENYLBORONIC ACID