|
|
| | 2-Methylthiophenylboronic acid Basic information |
| | 2-Methylthiophenylboronic acid Chemical Properties |
| Melting point | 77-83 °C (lit.) | | Boiling point | 215C | | density | 1,087g/cm | | refractive index | 1,423-1,425 | | storage temp. | Inert atmosphere,2-8°C | | Water Solubility | Slightly soluble in water | | form | Crystalline Powder | | pka | 8.50±0.58(Predicted) | | color | White | | BRN | 8309529 | | InChI | InChI=1S/C7H9BO2S/c1-11-7-5-3-2-4-6(7)8(9)10/h2-5,9-10H,1H3 | | InChIKey | QXBWTYBCNFKURT-UHFFFAOYSA-N | | SMILES | B(C1=CC=CC=C1SC)(O)O | | CAS DataBase Reference | 168618-42-6(CAS DataBase Reference) |
| | 2-Methylthiophenylboronic acid Usage And Synthesis |
| Chemical Properties | White crystalline powde | | Uses | suzuki reaction | | Uses | Reactant for:
- Palladium-catalyzed cross-coupling reactions
- Suzuki-Miyaura coupling reactions
| | Synthesis | Part A: Preparation of 2-methylthiophenylboronic acid. 2-Bromothioanisole (29.0 g, 143 mmol) was dissolved in anhydrous tetrahydrofuran (400 mL) and the solution was cooled to -75°C. n-Butyllithium (62.0 mL, 2.5 M hexane solution, 155 mmol) was added slowly over 50 minutes. After stirring for 25 min, triisopropyl borate (46 mL, 199 mmol) was added dropwise over 35 min. The cold bath was removed and the reaction mixture was stirred at room temperature for 16 hours. The resulting solution was cooled in an ice bath and 6 M hydrochloric acid (100 mL) was added. The mixture was stirred at room temperature for 5 hours and then concentrated to half the original volume. The concentrate was partitioned between ether and water. The organic layer was extracted with 2 M sodium hydroxide solution, subsequently acidified with 6 M hydrochloric acid, concentrated again, and extracted several times with ether. The ether extracts were combined, dried with sodium sulfate, filtered and the solvent evaporated to give a beige solid product (20.4 g, 85% yield).1H-NMR (CDCl3) δ: 8.01 (dd, 1H, J = 7.3, J' = 1.4), 7.53 (dd, 1H, J = 7.7, J' = 1.1), 7.43 (td, 1H, J = 7.3, J' = 1.8), 7.34 (td, 1H, J = 7.3, J'= 1.5), 6.22 (s, 2H), 2.50 (s, 3H). | | References | [1] Patent: EP946508, 2009, B1. Location in patent: Page/Page column 60
[2] Patent: EP1491187, 2004, A1. Location in patent: Page 26 |
| | 2-Methylthiophenylboronic acid Preparation Products And Raw materials |
|