BENZENESULFONAMIDE-3-BORONIC ACID PINACOL ESTER Chemical Properties

Boiling point:

447.1±47.0 °C(Predicted)

Density 

1.24±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

pka

10.04±0.60(Predicted)

Appearance

Off-white to light brown Solid

Safety Information

HS Code 

2935909099

BENZENESULFONAMIDE-3-BORONIC ACID PINACOL ESTER Usage And Synthesis

Synthesis

3-Bromobenzenesulfonamide (0.620 g, 2.63 mmol), potassium acetate (KOAc, 1.032 g, 10.52 mmol) and PdCl2(dppf)2 (0.100 g, 0.137 mmol) were used as raw materials, which were dissolved in dioxane (20 mL) under the protection of argon, and argon was blown up for 10 minutes to deoxygenate. Subsequently, bis(pinacolato)diboron (1.000 g, 3.94 mmol) was added to the reaction system, the reaction vessel was sealed, and the reaction was stirred at 110 °C for 24 hours. After completion of the reaction, the mixture was cooled to room temperature and filtered through diatomaceous earth. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate, gradient from 4:1 to 1:1) to afford the target product 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide (0.663 g, 89% yield) as a white solid. The product was characterized by NMR (DMSO-d6, HMDSO): δ 8.14 (ddd, J = 2.0, 1.1, 0.5 Hz, 1H), 7.93 (ddd, J = 7.9, 2.0, 1.3 Hz, 1H), 7.85 (td, J = 1.2, 7.4 Hz, 1H), 7.59 (ddd, J = 7.9, 7.4, 0.5 Hz, 1H), 1.32 (s, 12H).LCMS (ESI) m/z: 284.0 [M + H]+.

References

[1] Patent: WO2016/129983, 2016, A1. Location in patent: Page/Page column 35
[2] Patent: US2016/318895, 2016, A1. Location in patent: Paragraph 0339

BENZENESULFONAMIDE-3-BORONIC ACID PINACOL ESTER(486422-08-6)Related Product Information

• (3-AMINOSULPHONYL)BENZENEBORONIC ACID
• 2-Boronobenzenesulfonamide
• 4-SULFAMOYLPHENYLBORONIC ACID, PINACOL ESTER
• 4-(Aminosulfonyl)phenylboronic acid
• 4-[3-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-BENZENESULFONYL]-THIOMORPHOLINE
• 3-(N,N-Dimethylaminosulfonyl)phenylboronic acid pinacol ester
• BENZENESULFONAMIDE-3-BORONIC ACID PINACOL ESTER