ChemicalBook CAS DataBase List 4-AMINOMETHYLPHENYLBORONIC ACID, PINACOL ESTER, HCL

4-AMINOMETHYLPHENYLBORONIC ACID, PINACOL ESTER, HCL synthesis

11synthesis methods

Product Name:4-AMINOMETHYLPHENYLBORONIC ACID, PINACOL ESTER, HCL
CAS Number:138500-88-6
Molecular formula:C13H20BNO2
Molecular Weight:233.11

(4-PHTHALIMIDOMETHYLPHENYL)BORONIC ACID PINACOL ESTER

138500-87-5
55 suppliers
$19.00/250mg

4-AMINOMETHYLPHENYLBORONIC ACID, PINACOL ESTER, HCL

138500-88-6
94 suppliers
$19.00/100mg

Yield: 87%

Reaction Conditions:

with hydrazine hydrate in tetrahydrofuran for 12 h;Reflux;Solvent;

Steps:

[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanamine (4a).
Compound 3a (196 mg, 0.54 mmol) was added to a dry flask containing magnetic stir and dissolved in THF (5.50 mL). Afterwards, hydrazine hydrate (0.08 mL, 1.62 mmol) was added to the reaction mixture. The reaction was stirred under a reflux for 12 h. The resulting dried crude material was then re-suspended with chloroform (50.00 mL), filtered, and the filtrate was concentrated in vacuo. The crude material was purified by High Performance Liquid Chromatography (HPLC) to give the desired product 4a as a white solid (m.p. 85 °C) in 87% yield (111 mg); ¹H-NMR (CDCl₃) δ ppm 7.78 (d, J = 7.9 Hz, 2H),7.32 (d, J = 8.0 Hz, 2H), 3.88 (s, 2H), 1.34 (s, 12H); ¹³C-NMR (CDCl₃) δ ppm 136.72, 135.56, 127.18,84.11, 43.94, 25.02; ¹¹B-NMR (CD₃OD-d₄) δ ppm 30.90; HRMS (ESI, positive ion) (m/z): [M+H]⁺calcd for C₁₃H₂₀BNO₂, 234.1669; found, 234.1651.