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2,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine manufacturers
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| | 2,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine Basic information |
| Product Name: | 2,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine | | Synonyms: | 2,6-Dichloropyridine-4-boronic acid,pinacol ester;2,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl);2,6-Dichloropyridinyl-4-boronic acid pinacol ester;2,6-DICHLORO-4-(TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PYRIDINE;(2,6-DICHLOROPYRIDIN-4-YL)BORONIC ACID PINACOL ESTER;Pyridine, 2,6-dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-;2-(2,6-Dichloro-4-pyridyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2,6-DICHLORO-4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PYRIDINE ISO 9001：2015 REACH | | CAS: | 408492-27-3 | | MF: | C11H14BCl2NO2 | | MW: | 273.95 | | EINECS: | | | Product Categories: | Organic boronic acid | | Mol File: | 408492-27-3.mol |  |
| | 2,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine Chemical Properties |
| Melting point | 117-119°C | | Boiling point | 373.2±42.0 °C(Predicted) | | density | 1.24±0.1 g/cm3(Predicted) | | storage temp. | 2-8°C | | form | powder to crystal | | pka | -3.74±0.10(Predicted) | | color | White to Almost white | | InChI | 1S/C11H14BCl2NO2/c1-10(2)11(3,4)17-12(16-10)7-5-8(13)15-9(14)6-7/h5-6H,1-4H3 | | InChIKey | PEFDHAOFDBNZEQ-UHFFFAOYSA-N | | SMILES | CC1(C)OB(OC1(C)C)c2cc(Cl)nc(Cl)c2 | | CAS DataBase Reference | 408492-27-3 |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26 | | WGK Germany | 3 | | HS Code | 2933399990 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| | 2,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine Usage And Synthesis |
| Uses | 2,6-Dichloropyridine-4-boronic acid, pinacol ester | | Synthesis | General procedure for the synthesis of 2,6-dichloropyridine-4-boronic acid pinacol ester from 2,6-dichloropyridine and bis-boronic acid pinacol ester: Under nitrogen protection, 2,6-dichloropyridine (3 g, 20.3 mmol), 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl (5.92 g, 23.3 mmol), 1,10-phenanthroline (145 mg, 0.81 mmol) and chlorobis(1,5-cyclooctadiene)iridium(I) dimer (267 mg, 0.30 mmol) were dissolved in 1,2-dichloroethane (20 mL). After passing nitrogen for 5 minutes, the reaction mixture was heated at 100 °C for 1 hour. Upon completion of the reaction, the cooled mixture was poured into a mixture of ether (150 mL) and 4 M aqueous sodium hydroxide (200 mL) to separate the organic and aqueous phases. The aqueous phase was cooled with an ice bath and acidified with 5 M aqueous hydrochloric acid, and the resulting precipitate was filtered, washed with water and dried to afford 2,6-dichloropyridine-4-boronic acid pinacol ester (4.9 g, 17.9 mmol, 88% yield).LCMS (Method A): retention time 0.74 min; m/z 192,194 (as MH+ for boronic acid ionization).1H NMR ( 400 MHz, DMSO-d6) δ 1.28 (12H, s), 7.57 (2H, s). | | References | [1] Organic Letters, 2009, vol. 11, # 16, p. 3586 - 3589
[2] Journal of the American Chemical Society, 2015, vol. 137, # 25, p. 8058 - 8061
[3] Organic and Biomolecular Chemistry, 2014, vol. 12, # 37, p. 7318 - 7327
[4] Patent: WO2011/110575, 2011, A1. Location in patent: Page/Page column 73
[5] Journal of the American Chemical Society, 2018, vol. 140, # 49, p. 17197 - 17202 |
| | 2,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine Preparation Products And Raw materials |
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