5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)ISOINDOLIN-1-ONE Chemical Properties

Boiling point:

476.6±45.0 °C(Predicted)

Density 

1.16±0.1 g/cm3(Predicted)

storage temp. 

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

form 

solid

pka

13.95±0.20(Predicted)

Appearance

Off-white to light yellow Solid

Water Solubility 

Slightly soluble in water.

Safety Information

HS Code 

2933998090

5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)ISOINDOLIN-1-ONE Usage And Synthesis

Uses

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-one is a useful synthetic compound.

Synthesis

General procedure for the synthesis of 1-isoindolone-5-boronic acid pinacol ester from 5-bromo-2,3-dihydroisoindol-1-one and bipinacol ester: to an anhydrous solution of 5-bromo-2,3-dihydroisoindol-1-one (1 eq.) of dioxane (0.1 M) were added bis(pinacol) diboron (1.1 eq.), potassium acetate (3.5 eq.) and 1,1'-bis(diphenylphosphine ) ferrocene (dppf, 0.05 eq.). The reaction mixture was degassed with nitrogen for 20 minutes. Subsequently, dichloro(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) (PdCl2(dppf), 0.05 eq.) was added and the mixture was degassed again for 5 minutes. Under nitrogen protection, the reaction mixture was heated to 70 °C for 2 hours and then warmed to 120 °C to continue the reaction for 16 hours. After completion of the reaction, the mixture was partitioned between ethyl acetate (EtOAc) and water. The aqueous phase was further extracted with ethyl acetate, the organic phases were combined, dried over anhydrous magnesium sulfate (MgSO4), filtered and concentrated under reduced pressure. The residue was dissolved in dichloromethane (CH2Cl2) and hexane was added to precipitate the product. The resulting suspension was filtered and the brown powder was collected and dried and used without further purification. The yield of the product 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,3-dihydroisoindol-1-one was 94% and purity was 76% with boric acid (13%) as the major impurity. Mass spectrometry analysis (LC-MS, ESP): m/z 260.4 [2M+H]+, retention time (R/T) = 3.51 min.

References

[1] Patent: WO2008/23161, 2008, A1. Location in patent: Page/Page column 121-122
[2] Patent: WO2016/161145, 2016, A1. Location in patent: Paragraph 00746
[3] Patent: WO2016/180536, 2016, A1. Location in patent: Page/Page column 199
[4] Patent: US2009/286798, 2009, A1. Location in patent: Page/Page column 28-29
[5] Patent: WO2007/131991, 2007, A1. Location in patent: Page/Page column 91

5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)ISOINDOLIN-1-ONE(376584-62-2)Related Product Information

• 1-Ethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole
• 1-Isopropyl-1H-pyrazole-5-boronic acid, pinacol ester
• 4-Formyl-3-methylphenylboronic acid
• 5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)ISOINDOLIN-1-ONE