| Identification | Back Directory | [Name]
(4-Fluoro-2-(hydroxyMethyl)phenyl)boronic acid | [CAS]
1061223-45-7 | [Synonyms]
Tavaborole Impurity 14
(4-Fluoro-2-(hydroxyMethyl)phenyl)boronic acid
Boronic acid, B-[4-fluoro-2-(hydroxymethyl)phenyl]- | [Molecular Formula]
C7H8BFO3 | [MDL Number]
MFCD22205750 | [MOL File]
1061223-45-7.mol | [Molecular Weight]
169.95 |
| Chemical Properties | Back Directory | [Melting point ]
14-128°C | [Boiling point ]
361.2±52.0 °C(Predicted) | [density ]
1.35±0.1 g/cm3(Predicted) | [storage temp. ]
under inert gas (nitrogen or Argon) at 2-8°C | [solubility ]
Chloroform (Slightly), Ethyl Acetate (Slightly) | [form ]
Solid | [pka]
8.62±0.58(Predicted) | [color ]
White to Off-White |
| Hazard Information | Back Directory | [Uses]
4-Fluoro-2-(hydroxymethyl)phenylboronic Acid is a compound used in the preparation of 4,5-dihydro-1H-pyrazole derivatives as cholesterol 24 hydroxylase inhibitors. | [Synthesis]
GENERAL STEPS: To a solution of 2-bromo-5-fluorobenzyl alcohol (10.05 g, 49 mmol) in anhydrous ethanol (100 mL) was sequentially added NiCl2(dppp) (2.67 g, 4.9 mmol), tetrahydroxydiboron (6.62 g, 74 mmol), triphenylphosphine (0.01 mol), and N,N-diisopropylethylamine (25.7 mL. 148 mmol). The reaction system was degassed under nitrogen protection for 10 min. Subsequently, the reaction mixture was heated to reflux and stirred for 4 hours. After completion of the reaction, it was cooled to room temperature, diluted with water (100 mL) and extracted with ethyl acetate (3 × 50 mL). The organic phases were combined, dried with anhydrous sodium sulfate, and concentrated under reduced pressure to give the crude product 4-fluoro-2-(hydroxymethyl)phenylboronic acid (6), which was used directly in the next step of the reaction. After purification by column chromatography, the target compound was obtained (yield: 62%). | [References]
[1] Patent: WO2017/183043, 2017, A1. Location in patent: Page/Page column 33 |
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