4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulphonamide

Name	4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide
Synonyms	4-Boronobenzenesulfonamide,pinacol ester 4-Sulfamoylphenylboronic acid pinacol ester 4-SULFAMOYLPHENYLBORONIC ACID, PINACOL ESTER 4-Sulphamoylbenzeneboronic acid, pinacol ester BENZENESULFONAMIDE-4-BORONIC ACID PINACOL ESTER 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulphonamide 4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)benzenesulfonamide 3-hydroxy-2,3-dimethylbutan-2-yl hydrogen (4-sulfamoylphenyl)boronate
CAS	214360-51-7
InChI	InChI=1/C12H18BNO4S/c1-11(2)12(3,4)18-13(17-11)9-5-7-10(8-6-9)19(14,15)16/h5-8H,1-4H3,(H2,14,15,16)

Molecular Formula	C12H18BNO4S
Molar Mass	283.15
Density	1.24±0.1 g/cm3(Predicted)
Boling Point	427.1±47.0 °C(Predicted)
Flash Point	212.129°C
Vapor Presure	0mmHg at 25°C
pKa	10.00±0.10(Predicted)
Storage Condition	under inert gas (nitrogen or Argon) at 2-8°C
Refractive Index	1.543

Application	Phenylsulfonamido-4-boric acid is a boric acid derivative, boric acid derivatives are widely used in organic synthesis for the formation of carbon-carbon bonds. In Suzuki coupling, aryl halides and boric acid aryl or vinyl ester or boric acid are coupled using Pd(PPh3)4.
Uses	Phenylsulfonamido-4-boric acid is a carboxylic acid derivative, mainly used as a pharmaceutical intermediate.
preparation	potassium acetate (2.5g, 24.4 mmol) is added to a solution of 4-bromobenzenesulfonamide (2.00g, 9.32 mmol) and bis (pinacol) diboron (2.40g, 9.32 mmol) in DMSO(20 ml) and degas the mixture for 45 minutes. Then [1,1 '-bis (diphenylphosphino) ferrocene] dichloropalladium (II)(220 mg, 0.26 mmol) was added and the mixture was heated to 90°C for 16 hours. Once cooled, the reaction mixture was diluted with EtOAc(30 ml), washed with water (3 × 30 ml), dried with MgSO4 and concentrated under vacuum. The residue was ground from Et2O(50 ml) and HCl(1M,50 ml), the resulting solid was dissolved in CH2Cl2(30 ml) and filtered through a silicone pad cleaned with Et2O, and then concentrated to obtain phenylsulfonamido-4-boric acid as an off-white solid, with a 13% yield of 550 mg.

Last Update：2024-04-09 21:11:58

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CAS: 214360-51-7
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