3,5-Dimethoxyphenylboronic acid Chemical Properties

Melting point:

202-207 °C

Boiling point:

371.6±52.0 °C(Predicted)

Density 

1.19±0.1 g/cm3(Predicted)

Flash point:

81℃

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Soluble in methanol.

pka

7.67±0.10(Predicted)

form 

powder to crystal

color 

White to Light yellow to Light orange

CAS DataBase Reference

192182-54-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

WGK Germany 

3

Hazard Note 

Irritant/Keep Cold

HazardClass 

IRRITANT, KEEP COLD

HS Code 

29163990

3,5-Dimethoxyphenylboronic acid Usage And Synthesis

Chemical Properties

Gray to white solid

Uses

3,5-Dimethoxyphenylboronic acid is a useful reagent for palladium-catalyst and Suzuki-Miyaura cross coupling reactions.

Uses

Reactant for:

• Palladium-catalyzed coupling reactions
• Preparation of benzopyranone derivatives as positive GABAA receptor modulators
• Preparation of aryl alkenes via three-component coupling catalyzed by palladium
• Suzuki-Miyaura coupling
• Rhodium catalyzed cyanation with N-cyano-N-phenyl-p-methylbenzenesulfonamide
• Preparation of bisphosphonate inhibitors of human farnesyl pyrophosphate synthase

Uses

suzuki reaction

Synthesis

1. Synthesis of 3,5-dimethoxyphenylboronic acid: After cooling the flame-dried reaction vessel under argon protection, 3,5-dimethoxybromobenzene (3 g, 13.82 mmol) and anhydrous tetrahydrofuran (36 ml) were added. The mixture was stirred until a clarified solution was formed. Subsequently, the reaction mixture was cooled to -78 °C and maintained at this temperature for 15 minutes. n-Butyllithium (10.92 ml, 2.1 M hexane solution) was slowly added and the reaction mixture continued to be stirred at -78 °C for 30 minutes. Then, triisopropyl borate (5.2 g, 27.64 mmol) was added dropwise and the reaction was continuously stirred at -78°C for 2 hours. After completion of the reaction, it was slowly warmed up to room temperature and acidified with 2 M sulfuric acid solution to pH 2. The reaction mixture was extracted with ethyl acetate, the organic phases were combined, dried with anhydrous magnesium sulfate and concentrated under reduced pressure to remove the solvent. The crude product was purified by recrystallization from petroleum ether to give 3,5-dimethoxyphenylboronic acid in 92% yield.

References

[1] Patent: WO2008/118802, 2008, A1. Location in patent: Page/Page column 25-26

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