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| | 2,5-Bis-Thiopheneboronic acid pinacol ester Basic information |
| Product Name: | 2,5-Bis-Thiopheneboronic acid pinacol ester | | Synonyms: | 2,5-Bis-Thiopheneboronic acid pinacol ester;Thiophene-2,5-diboronic acid bis(pinacol) ester;2,5-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene;2,5-Thiophenediboronic acid bis(pinacol) ester;Bis(4,4,5,5-tetramethyl-1,3-dioxaborolane)-2,5-thiophene;Thiophene-2,5-diboronic acids pinacol ester;Thiophene-2,5-diboronic acid bis(pinacol) ester 99% (GC);2,2'-(2,5-Thiophenediyl)bis[4,4,5,5-tetramethyl-1,3,2-dioxaborolane] | | CAS: | 175361-81-6 | | MF: | C16H26B2O4S | | MW: | 336.06 | | EINECS: | | | Product Categories: | Thiophene (TH);Organoborons;Thiophene | | Mol File: | 175361-81-6.mol |  |
| | 2,5-Bis-Thiopheneboronic acid pinacol ester Chemical Properties |
| Melting point | 216-220℃ | | Boiling point | 434.3±30.0 °C(Predicted) | | density | 1.08±0.1 g/cm3(Predicted) | | storage temp. | Keep in dark place,Inert atmosphere,Store in freezer, under -20°C | | form | powder | | color | White to Almost white | | InChI | InChI=1S/C16H26B2O4S/c1-13(2)14(3,4)20-17(19-13)11-9-10-12(23-11)18-21-15(5,6)16(7,8)22-18/h9-10H,1-8H3 | | InChIKey | AOJXAKMKFDBHHT-UHFFFAOYSA-N | | SMILES | C1(B2OC(C)(C)C(C)(C)O2)SC(B2OC(C)(C)C(C)(C)O2)=CC=1 |
| WGK Germany | 3 | | HS Code | 2934999090 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Aquatic Chronic 4 |
| | 2,5-Bis-Thiopheneboronic acid pinacol ester Usage And Synthesis |
| Uses | Diboronic acid ester thiophene monomer for polymerization by Suzuki coupling; used for OPV and OFET applications. | | Synthesis | To a solution of 2,5-dibromothiophene (2.0 g, 8.3 mmol) in anhydrous THF (40 mL) was slowly added n-butyllithium (n-BuLi, 15 mL, 1.6 M hexanes solution, 25 mmol) dropwise at -78 °C and the reaction mixture was stirred for 1 hour keeping the temperature at -78 °C. Subsequently, tributyl borate (6.4 mL, 25 mmol) was added to the reaction mixture at the same temperature and the reaction system was gradually warmed to room temperature. After continued stirring for 2 hours, pinacol (3.8 g, 33 mmol) and acetic acid (1.4 mL, 25 mmol) were added sequentially and the resulting mixture was stirred and reacted for 14 hours at room temperature. After completion of the reaction, the reaction solution was filtered through a diatomaceous earth pad and the filtrate was concentrated under reduced pressure. The residue (brown solid) was purified by recrystallization from a solvent mixture of ethyl acetate and hexane to afford the target product dipinacol ester of thiophene-2,5-diboronic acid (2.0 g, 75% yield) as a white solid. | | References | [1] Chem, 2016, vol. 1, # 1, p. 91 - 101 |
| | 2,5-Bis-Thiopheneboronic acid pinacol ester Preparation Products And Raw materials |
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