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Product Name:2-(1-Benzothiophen-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 95%
CAS:501945-71-7
Purity:95% Package:1G
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| | 2-(1-BENZOTHIOPHEN-5-YL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE Basic information |
| Product Name: | 2-(1-BENZOTHIOPHEN-5-YL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE | | Synonyms: | 2-(1-BENZOTHIOPHEN-5-YL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE;2-(benzothiophen-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-(1-Benzothiophen-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane ,95%;2-(1-benzothiophen-5-yl)-4;2-dioxaborolane;Benzo[b]thiophene, 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-;Benzo[b]thiophene-5-boronic Acid Pinacol Ester;2-(benzo[b]thiophen-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane | | CAS: | 501945-71-7 | | MF: | C14H17BO2S | | MW: | 260.16 | | EINECS: | | | Product Categories: | | | Mol File: | 501945-71-7.mol |  |
| | 2-(1-BENZOTHIOPHEN-5-YL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE Chemical Properties |
| Melting point | 118 °C | | storage temp. | under inert gas (nitrogen or Argon) at 2–8 °C | | Appearance | White to off-white Solid |
| | 2-(1-BENZOTHIOPHEN-5-YL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE Usage And Synthesis |
| Synthesis | 5-Bromobenzo[b]thiophene (49 g, 7.0 mmol) was dissolved in DMSO (40 mL). To this solution, bis(pinacolato)diboron (7 mmol), PdCl2(dppf)-CH2Cl2 (0.33 mmol) and KOAc (20 mmol) were added sequentially. After displacement of the reaction system with nitrogen, the reaction mixture was heated to 80 °C with stirring. After maintaining the reaction at this temperature for 3 h, the reaction mixture was cooled to room temperature. Water (66 mL) was added to the reaction mixture and the aqueous layer was subsequently extracted with EtOAc (3 x 66 mL). The organic layers were combined, dried with anhydrous Na2SO4, filtered and concentrated. Finally, purification by fast column chromatography (silica gel, 0-5% Et2O/pentane as eluent) afforded 2-(1-benzothiophen-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 1.56 g in 86% yield. | | References | [1] Patent: WO2004/9086, 2004, A1. Location in patent: Page/Page column 49
[2] Patent: US2006/52378, 2006, A1. Location in patent: Page/Page column 104
[3] Journal of the American Chemical Society, 2017, vol. 139, # 24, p. 8267 - 8276
[4] Angewandte Chemie - International Edition, 2018, vol. 57, # 34, p. 10999 - 11003
[5] Angew. Chem., 2018, # 130, p. 11165 - 11169,5 |
| | 2-(1-BENZOTHIOPHEN-5-YL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE Preparation Products And Raw materials |
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