| Identification | More | [Name]
2-Methoxyl-5-pyridineboronic acid pinacol ester | [CAS]
445264-61-9 | [Synonyms]
2-METHOXY-5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PYRIDINE
2-METHOXY-5-PYRIDINEBORONIC ACID, PINACOL ESTER
2-methoxyl-5-pyridineboronic acid pinacol ester
2-METHOXYPYRIDINE-5-BORONIC ACID PINACOL ESTER
6-METHOXYPYRIDINE-3-BORONIC ACID, PINACOL ESTER
2-Methoxy-5-pyridineboronic acid pinacol ester, 2-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine | [Molecular Formula]
C12H20BNO4 | [MDL Number]
MFCD05663858 | [Molecular Weight]
253.1 | [MOL File]
445264-61-9.mol |
| Chemical Properties | Back Directory | [Melting point ]
47-51 °C(lit.) | [Boiling point ]
102°C/0.08mmHg(lit.) | [density ]
1.06±0.1 g/cm3(Predicted) | [Fp ]
216 °F
| [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [Water Solubility ]
Soluble in water | [form ]
powder to crystal | [pka]
3.39±0.12(Predicted) | [color ]
White to Almost white | [InChI]
1S/C12H18BNO3/c1-11(2)12(3,4)17-13(16-11)9-6-7-10(15-5)14-8-9/h6-8H,1-5H3 | [InChIKey]
QOGNDJLSYMJGPP-UHFFFAOYSA-N | [SMILES]
COc1ccc(cn1)B2OC(C)(C)C(C)(C)O2 | [CAS DataBase Reference]
445264-61-9(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/38:Irritating to eyes and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [HS Code ]
2933399990 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2 |
| Hazard Information | Back Directory | [Uses]
(2-Methoxypyridin-5-yl)boronic Acid Pinacol Ester is used in the design and synthesis of oxazolidinone antibacterial agents. As well, it is used in the synthesis of [3,2-b]pyridines. | [Uses]
2-Methoxypyridine-5-boronic acid pinacol ester is used in the design and synthesis of oxazolidinone antibacterial agents. As well, it is used in the synthesis of [3,2-b]pyridines.
| [Synthesis]
Step 1: 5-bromo-2-methoxypyridine (55 g, 0.29 mol), pinacol ester of bisboronic acid (90 g, 0.35 mol), potassium acetate (57 g, 0.58 mol) and bis(triphenylphosphine)palladium(II) chloride (2.2 g, 3 mmol) were dissolved in anhydrous dioxane (500 mL) under nitrogen protection. The reaction mixture was heated and stirred at 108 °C overnight. Upon completion of the reaction, the mixture was concentrated and purified by column chromatography using hexane/ethyl acetate as eluent to afford pinacol ester of 6-methoxypyridine-3-boronic acid (58 g, 84% yield). | [References]
[1] Patent: US9249156, 2016, B2. Location in patent: Page/Page column 36
[2] Patent: WO2018/85342, 2018, A1. Location in patent: Page/Page column 26; 28
[3] Patent: WO2014/186035, 2014, A1. Location in patent: Page/Page column 151
[4] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 12, p. 2496 - 2500
[5] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 19, p. 6477 - 6485 |
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