4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-trityl-1H-pyrazole

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4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-trityl-1H-pyrazole Basic information
Product Name:4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-trityl-1H-pyrazole
Synonyms:4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-trityl-1H-pyrazole;4-(tetraMethyl-1,3,2-dioxaborolan-2-yl)-1-(triphenylMethyl)-1H-pyrazole;1-Trityl-1H-pyrazole-4-boronic acid pinacol ester;4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-trityl-pyrazole;4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triphenylmethyl)pyrazole;1H-Pyrazole, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triphenylmethyl)-;4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-trityl-1H...;4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triphenylmethyl)-1H-pyrazole
CAS:863238-73-7
MF:C28H29BN2O2
MW:436.35
EINECS:
Product Categories:
Mol File:863238-73-7.mol
4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-trityl-1H-pyrazole Structure
4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-trityl-1H-pyrazole Chemical Properties
Boiling point 587.3±50.0 °C(Predicted)
density 1.07±0.1 g/cm3 (20 ºC 760 Torr)
storage temp. under inert gas (nitrogen or Argon) at 2-8°C
pka1.37±0.10(Predicted)
AppearanceWhite to off-white Solid
Safety Information
MSDS Information
4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-trityl-1H-pyrazole Usage And Synthesis
Synthesis
4-BROMO-1-TRITYL-1H-PYRAZOLE

95162-14-4

Bis(pinacolato)diboron

73183-34-3

4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-trityl-1H-pyrazole

863238-73-7

The general procedure for the synthesis of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-trityl-1H-pyrazole from 1-trityl-4-bromopyrazole and bis(pinacolato)diboron was carried out in the following manner: under stirring conditions, 5.0 g (12.8 mmol) of 1-trityl-4-bromo-1H-pyrazole, 9.8 g (38.6 mmol, 3.0 eq.) bis(pinacolato)diboron, 1.0 g (1.3 mmol, 10 mol%) of PdCl2 (dppf), and 6.3 g (64.2 mmol, 5.0 eq.) of potassium acetate were dissolved in 30 mL of DMF and heated to react for 16 hr at 80 °C. After completion of the reaction, the mixture was diluted with water and the product was extracted with dichloromethane. The organic layer was sequentially washed with brine, dried over anhydrous sodium sulfate, and finally purified by fast chromatography to afford 5.1 g (91% yield) of the target compound 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-trityl-1H-pyrazole.

References[1] Patent: US2008/261975, 2008, A1. Location in patent: Page/Page column 12
[2] Journal of Organic Chemistry, 2018, vol. 83, # 5, p. 2954 - 2958
[3] Patent: US2009/82403, 2009, A1. Location in patent: Page/Page column 81
[4] Patent: US2007/105904, 2007, A1. Location in patent: Page/Page column 78-79
4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-trityl-1H-pyrazole Preparation Products And Raw materials
Raw materials4-Bromo-1-trityl-1H-pyrazole-->Pinacol-->Triisopropyl borate-->Bis(pinacolato)diboron-->N,N-Dimethylformamide-->Potassium Acetate
Tag:4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-trityl-1H-pyrazole(863238-73-7) Related Product Information
4-Pyrazoleboronic acid pinacol ester 1-Methyl-4-pyrazole boronic acid pinacol ester 1-Benzyl-1H-pyrazole-4-boronic acid pinacol ester 1H-Pyrazole, 1-(1-Methylethyl)-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)- 1-Boc-pyrazole-4-boronic acid pinacol ester 1-Ethyl-1H-pyrazole-4-boronic acid, pinacol ester