4,4,5,5-Tetramethyl-2-(4-vinylphenyl)-1,3,2-dioxaborolane manufacturers
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| | 4,4,5,5-Tetramethyl-2-(4-vinylphenyl)-1,3,2-dioxaborolane Basic information |
| Product Name: | 4,4,5,5-Tetramethyl-2-(4-vinylphenyl)-1,3,2-dioxaborolane | | Synonyms: | 4,4,5,5-Tetramethyl-2-(4-vinylphenyl)-1,3,2-dioxaborolane;1,3,2-Dioxaborolane, 2-(4-ethenylphenyl)-4,4,5,5-tetramethyl-;4,4,5,5-Tetramethyl-2-(4-vinylphenyl)-1,3,2-dioxaborolane,97%(stabilized with TBC);4-Ethenylbenzeneboronic acid pinacol ester;4-Vinylbenzeneboronic acid pinacol ester;4-ethylenebenzeneboronic acidolester | | CAS: | 870004-04-9 | | MF: | C14H19BO2 | | MW: | 230.11 | | EINECS: | | | Product Categories: | | | Mol File: | 870004-04-9.mol |  |
| | 4,4,5,5-Tetramethyl-2-(4-vinylphenyl)-1,3,2-dioxaborolane Chemical Properties |
| Boiling point | 323.5±21.0 °C(Predicted) | | density | 0.98±0.1 g/cm3(Predicted) | | storage temp. | under inert gas (nitrogen or Argon) at 2–8 °C | | solubility | Chloroform (Sparingly), Hexane (Very Slightly) | | form | Oil to Low-Melting Solid | | color | White to Brown | | Stability: | Hygroscopic | | InChI | InChI=1S/C14H19BO2/c1-6-11-7-9-12(10-8-11)15-16-13(2,3)14(4,5)17-15/h6-10H,1H2,2-5H3 | | InChIKey | ONBKTEDYJFZZCU-UHFFFAOYSA-N | | SMILES | O1C(C)(C)C(C)(C)OB1C1=CC=C(C=C)C=C1 |
| | 4,4,5,5-Tetramethyl-2-(4-vinylphenyl)-1,3,2-dioxaborolane Usage And Synthesis |
| Synthesis | General methodology: synthesis of 4,4,5,5-tetramethyl-2-(4-vinylphenyl)-1,3,2-dioxaborolane (4a). In anhydrous THF (50 mL), 4-vinylphenylboronic acid (3a, 1.00 g, 6.76 mmol), pinacol (802 mg, 6.80 mmol) and a small amount of magnesium sulfate desiccant were added and the reaction was stirred for 2 h at room temperature. After completion of the reaction, the solid impurities were removed by filtration, and the filtrate was concentrated under reduced pressure to afford the target product 4a (1.55 g, quantitative yield) as a colorless liquid. The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3): δ 7.76 (d, 2H, J = 8.0 Hz), 7.40 (d, 2H, J = 8.0 Hz), 6.72 (dd, 1H, J1 = 11.0 Hz, J2 = 17.6 Hz), 5.81 (d, 1H, J = 17.6 Hz), 5.29 (d, 1H, J = 11.0 Hz), 1.81 (d, 1H, J = 11.0 Hz), 1.29 (d, 1H, J = 11.0 Hz). 11.0 Hz), 1.34 (s, 12H).13C NMR (100 MHz, CDCl3) data: δ 140.2, 136.9, 135.0 (2C), 125.5 (2C), 114.9, 83.8 (2C), 24.9 (4C). The measured value of m/z 253.1384 by high-resolution mass spectrometry (HRMS-ES) is consistent with the calculated value [C14H19B2Na]+ 253.1376. | | References | [1] Tetrahedron Letters, 2013, vol. 54, # 10, p. 1211 - 1217
[2] Journal of Organic Chemistry, 2016, vol. 81, # 17, p. 8050 - 8060
[3] Journal of the American Chemical Society, 2007, vol. 129, # 34, p. 10348 - 10349
[4] Angewandte Chemie - International Edition, 2018, vol. 57, # 31, p. 9785 - 9789
[5] Angew. Chem., 2018, vol. 130, # 31, p. 9933 - 9937,5 |
| | 4,4,5,5-Tetramethyl-2-(4-vinylphenyl)-1,3,2-dioxaborolane Preparation Products And Raw materials |
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