4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one
- Product Name
- 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one
- CAS No.
- 1150271-44-5
- Chemical Name
- 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one
- Synonyms
- Oxindole-4-boronic acid picol ester;Oxindole-4-boronic acid pinacal ester;Oxindole-4-boronic acid pinacol ester;2-Oxoindoline-4-boronic Acid Pinacol Ester;(2-OXOINDOLIN-4-YL)BORONIC ACID PINACOL ESTER;4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one;4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-dihydroindol-2-one;1,3-Dihydro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-indol-2-one;2H-Indol-2-one, 1,3-dihydro-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-
- CBNumber
- CB02490513
- Molecular Formula
- C14H18BNO3
- Formula Weight
- 259.11
- MOL File
- 1150271-44-5.mol
4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one Property
- Boiling point:
- 427.9±45.0 °C(Predicted)
- Density
- 1.16±0.1 g/cm3(Predicted)
- storage temp.
- under inert gas (nitrogen or Argon) at 2-8°C
- pka
- 14.17±0.20(Predicted)
- form
- solid
- color
- Brown
Safety
- HS Code
- 2933998090
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H317May cause an allergic skin reaction
H319Causes serious eye irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P280Wear protective gloves/protective clothing/eye protection/face protection.
N-Bromosuccinimide Price
- Product number
- T204895
- Product name
- 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one
- Packaging
- 100mg
- Price
- $65
- Updated
- 2021/12/16
- Product number
- OR361514
- Product name
- Oxindole-4-boronic acid, pinacol ester
- Packaging
- 250mg
- Price
- $90
- Updated
- 2021/12/16
- Product number
- Z7622
- Product name
- Oxindole-4-boronicacidpinacolester
- Packaging
- 250mg
- Price
- $155
- Updated
- 2021/12/16
- Product number
- 093316
- Product name
- 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one
- Purity
- 95+%
- Packaging
- 250mg
- Price
- $567
- Updated
- 2021/12/16
- Product number
- BOR0002659
- Product name
- 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)INDOLIN-2-ONE
- Purity
- 95.00%
- Packaging
- 100MG
- Price
- $788.29
- Updated
- 2021/12/16
4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one Chemical Properties,Usage,Production
Synthesis
99365-48-7
73183-34-3
1150271-44-5
The general procedure for the synthesis of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indol-2-one from 4-bromoindolone and pinacol bis(boronic acid) ester is as follows: 1. in a dry reaction vial, 4-bromodihydroindol-2-one (1.038 g, 4.90 mmol), pinacol ester of bisboronic acid (1.903 g, 7.49 mmol), [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride complexed with dichloromethane (0.601 g, 0.73 mmol) and potassium acetate (1.480 g , 15.08 mmol) in a solution of 1,4-dioxane (30 mL). 2. The reaction mixture was stirred at 110 °C for 2 hours. 3. After completion of the reaction, the mixture was cooled to room temperature and filtered through a cartridge containing 10 g of diatomaceous earth. 4. The filter cake was washed with ethyl acetate (3 x 30 mL), the filtrates were combined and concentrated under vacuum to give a brown liquid. 5. The crude product was dissolved in dichloromethane (about 10 mL) and purified by passing through a 100 g SNAP silica gel column using a Biotage SP4 semi-automated fast column chromatography system eluting with a gradient of 20% to 50% ethyl acetate in cyclohexane solution. 6. Fractions containing the target product were collected, combined and concentrated under vacuum. 7. The concentrate was dissolved in dichloromethane (~10 mL), transferred to a pre-weighed vial and the solvent was evaporated under a stream of nitrogen. 8. The residue was ground with ether (5 x 5 mL) and the supernatant was precipitated by decantation each time and finally dried under vacuum under a stream of nitrogen to afford the milky white solid product 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dihydroindol-2-one (941.8 mg, 3.63 mmol, 74% yield). Product characterization: LCMS (2 min form): retention time Rt = 0.93 min, [MH]+ = 260.3.
References
[1] Patent: WO2017/174621, 2017, A1. Location in patent: Page/Page column 88
[2] Patent: WO2017/202742, 2017, A1. Location in patent: Page/Page column 42; 43; 97; 98
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