3-METHYL-4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZOIC ACID Chemical Properties

Boiling point:

394.1±35.0 °C(Predicted)

Density 

1.13±0.1 g/cm3(Predicted)

storage temp. 

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

pka

4.16±0.10(Predicted)

form 

solid

color 

Red-brown

Safety Information

HS Code 

2931900090

3-METHYL-4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZOIC ACID Usage And Synthesis

Synthesis

4-Bromo-3-methylbenzoic acid (1 g, 4.65 mmol) and pinacol ester of bisboronic acid (1.77 g, 6.97 mmol) were used as raw materials in the [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride complex with dichloromethane (1:1) (379 mg, 0.46 mmol) and potassium acetate (2.3 g, 23.2 mmol) in the in N,N-dimethylformamide (23 mL) in the presence of potassium acetate (2.3 g, 23.2 mmol) were heated in a microwave reaction system (Biotage Initiator sixty) at 120 °C for 15 min. Upon completion of the reaction, the solvent was removed by evaporation under reduced pressure and the residue was suspended in a 2N HCl/ethyl acetate mixture (40 mL, 1:1 v/v). Filtered through sintered glass, the aqueous phase was extracted with ethyl acetate. The organic layers were combined, washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by fast column chromatography on silica gel, using hexane/ethyl acetate (7:3) as eluent, to afford 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid (1.1 g, yield 90%) as a white solid.1H-NMR (CDCl3) δ: 1.36 (s, 12H), 2.59 (s, 3H), 7.85-7.90 (m, 3H).

References

[1] Journal of Medicinal Chemistry, 2009, vol. 52, # 17, p. 5531 - 5545
[2] Patent: WO2007/96072, 2007, A2. Location in patent: Page/Page column 36
[3] Patent: WO2008/51493, 2008, A2. Location in patent: Page/Page column 145

3-METHYL-4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZOIC ACID(269409-74-7)Related Product Information

• (4-FORMYL-2-METHYLPHENYL)BORONIC ACID
• 3-METHYL-4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZOIC ACID
• 3-METHYL-4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZALDEHYDE
• 4-(Methoxycarbonyl)-2-methylphenylboronic acid pinacol ester
• (4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol
• (2-METHYL-4-CARBOXYPHENYL)BORONIC ACID
• 2-METHYLPHENYLBORONIC ACID, PINACOL ESTER
• 2,4-DIMETHYLPHENYLBORONIC ACID
• 4-Carboxylphenylboronic acid pinacol ester