| Identification | Back Directory | [Name]
(N-AcrylaMidophenyl)boronic acid pinacol ester | [CAS]
874363-18-5 | [Synonyms]
N,N'-(1,2-DIHYDROXYETHYLENE)BISACRYLAMIDE
3-Acrylamidophenylboronic Acid Pinacol Ester
(N-AcrylaMidophenyl)boronic acid pinacol ester
3-(N-Acrylamidophenyl)boronic acid pinacol ester
2-(3-Acrylamidophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
N-[3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acrylamide
2-Propenamide,N-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]- | [Molecular Formula]
C15H22BNO4 | [MDL Number]
MFCD22493996 | [MOL File]
874363-18-5.mol | [Molecular Weight]
291.15 |
| Chemical Properties | Back Directory | [Melting point ]
160 °C | [Boiling point ]
437.4±37.0 °C(Predicted) | [density ]
1.07±0.1 g/cm3(Predicted) | [storage temp. ]
under inert gas (nitrogen or Argon) at 2-8°C | [form ]
powder to crystal | [pka]
13.74±0.70(Predicted) | [color ]
White to Light yellow |
| Hazard Information | Back Directory | [Synthesis]
1. 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (0.300 g, 1.37 mmol) and N,N-diisopropylethylamine (DIEA, 0.311 mL, 1.78 mmol) were dissolved in dichloromethane (DCM, 9.1 mL) in the conditions of an ice bath.
2. Acryloyl chloride (0.117 mL, 1.44 mmol) was slowly added to the above solution, keeping the reaction system in an ice bath.
3. The reaction mixture was transferred to room temperature and stirring was continued for 40 minutes.
4. Upon completion of the reaction, the reaction mixture was concentrated by rotary evaporator.
5. The concentrated residue was purified by silica gel column chromatography (24 g silica gel) using a solvent mixture of ethyl acetate-hexane (gradient elution, 15-40%) as eluent.
6. The target fraction was collected and concentrated to afford N-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acrylamide as a white solid (0.292 g, 78% yield).
7. Mass spectrometry showed m/z 270 (M + H). | [References]
[1] Patent: WO2016/65236, 2016, A1. Location in patent: Page/Page column 108
[2] Patent: US2016/115126, 2016, A1. Location in patent: Paragraph 0505
[3] Journal of Polymer Science, Part A: Polymer Chemistry, 2012, vol. 50, # 16, p. 3373 - 3382 |
|
|