4-Benzyloxy-3-methylbenzeneboronic acid Chemical Properties

Melting point:

102-106

Boiling point:

431.6±55.0 °C(Predicted)

Density 

1.17±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

form 

powder to crystal

pka

8.74±0.17(Predicted)

color 

White to Almost white

CAS DataBase Reference

338454-30-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36

HazardClass 

IRRITANT

HS Code 

29310095

4-Benzyloxy-3-methylbenzeneboronic acid Usage And Synthesis

Uses

suzuki reaction

Synthesis

General procedure for the synthesis of 4-benzyloxy-3-methylbenzeneboronic acid from 2-benzyloxy-5-bromotoluene: 4-bromo-1-benzyloxy-2-methylbenzene (6.9 g, 25 mmol) was dissolved in molecularly sieve-dried tetrahydrofuran (37.5 mL) and the solution was cooled to -78 °C. A n-hexane solution of 1.6 M n-butyllithium (17 mL, 27.5 mmol) was added slowly and dropwise over a period of 30 min, keeping the reaction temperature from exceeding -70 °C. After continued stirring at this temperature for 10 min, trimethyl borate (8.3 mL, 75 mmol) was added dropwise over 25 min below -70 °C. The reaction mixture was allowed to warm slowly to room temperature and stirred overnight. The reaction mixture was then cooled to 0 °C and aqueous 1 N hydrochloric acid was added dropwise. The reaction mixture was diluted with water and ethyl acetate to separate the organic and aqueous phases, and the aqueous phase was then extracted with ethyl acetate. The organic phases were combined, washed sequentially with water and saturated aqueous sodium chloride solution, dried with magnesium sulfate, filtered and concentrated. 4-Benzyloxy-3-methylphenylboronic acid 3.95 g (yield 65%) was obtained as a white powder. Mass spectrum (ISN): 301.2 (M-H)-.

References

[1] Patent: US6821980, 2004, B1. Location in patent: Page column 28
[2] Chemistry - A European Journal, 2000, vol. 6, # 20, p. 3821 - 3837

4-Benzyloxy-3-methylbenzeneboronic acid(338454-30-1)Related Product Information

• 2-(BENZYLOXY)-5-METHYLPHENYLBORONIC ACID
• 4-Benzyloxy-2-methylphenylboronic acid
• 4-(2'-CHLOROBENZYLOXY)-3,5-DIMETHYLPHEN&
• 2-[4-Benzyloxy-3-(trifluoromethyl)phenyl]-5,5-dimethyl-1,3,2-dioxaborinane
• 4-Benzyloxy-3,5-dimethylphenylboronic acid
• 2-Benzyloxy-5-(4,4,6-trimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile
• (2-(benzyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)(pyrrolidin-1-yl)methanone
• 4-(3'-CHLOROBENZYLOXY)-3,5-DIMETHYLPHEN&
• 4-BENZYLOXY-3-CHLORO-5-METHYLPHENYLBORONIC ACID
• 4-BENZYLOXY-3-FORMYLPHENYLBORONIC ACID
• 4-Benzyloxy-3-methylbenzeneboronic acid
• 2-(4-(Benzyloxy)-3-(trifluoromethyl)phenyl)-4,4,6-trimethyl-1,3,2-dioxaborinane
• 4-(4'-CHLOROBENZYLOXY)-3,5-DIMETHYLPHEN&
• 2-Benzyloxy-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile
• 2-[4-Benzyloxy-3-(1,3-dioxan-2-yl)phenyl]-5,5-dimethyl-1,3,2-dioxaborinane
• 2-[4-Benzyloxy-3-(1,3-dioxan-2-yl)phenyl]-4,4,6-trimethyl-1,3,2-dioxaborinane