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507462-88-6

507462-88-6 Structure

507462-88-6 Structure
IdentificationBack Directory
[Name]

3-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol
[CAS]

507462-88-6
[Synonyms]

4-Hydroxy-2-methoxyphenylboronic acid pinacol ester
3-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol
Phenol, 3-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-
[Molecular Formula]

C13H19BO4
[MDL Number]

MFCD16994337
[MOL File]

507462-88-6.mol
[Molecular Weight]

250.1
Chemical PropertiesBack Directory
[Boiling point ]

386.4±32.0 °C(Predicted)
[density ]

1.11±0.1 g/cm3(Predicted)
[storage temp. ]

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

9.28±0.35(Predicted)
[Appearance]

White to off-white Solid
Safety DataBack Directory
[Symbol(GHS) ]


GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H315-H319-H335
[Precautionary statements ]

P261-P305+P351+P338
Hazard InformationBack Directory
[Uses]

3-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol is a useful reagent in the preparation of ethylidenedihydroindolones, that functions as potential checkpoint 1 kinase inhibitors for abrogating the G2 DNA damage checkpoint arrest.
[Synthesis]

4-Bromo-3-methoxyphenol

102127-34-4

Bis(pinacolato)diboron

73183-34-3

3-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

507462-88-6

4-Bromo-3-methoxyphenol (5 g, 24.75 mmol) and pinacol ester of bisboronic acid (9.43 g, 37.13 mmol) were dissolved in dioxane (50 mL), and anhydrous potassium acetate (6.1 g, 74.25 mmol) and [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane complex (2 g. 2.47 mmol). The reaction mixture was heated to 80 °C and stirred for 16 h under nitrogen protection. After completion of the reaction, it was cooled to room temperature, the reaction mixture was diluted with ethyl acetate (50 mL) and filtered through diatomaceous earth. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (eluent ratio of petroleum ether: ethyl acetate = 1:1) to afford the target product, 3-methoxy-4-boronic acid pinacol ester phenol (17-c), as a pale yellow solid (2.8 g, 45% yield). The product was analyzed by mass spectrometry (LC-MS, ESI): m/z = 251 [M + H]+.

[References]

[1] Patent: US2018/208604, 2018, A1. Location in patent: Paragraph 0283-0284
[2] Patent: WO2014/28459, 2014, A1. Location in patent: Page/Page column 107; 108
Spectrum DetailBack Directory
[Spectrum Detail]

3-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol(507462-88-6)1HNMR
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