Name | 2-methylpyridine-3-boronic acid |
Synonyms | 3-Borono-2-methylpyridine 2-PICOLINE-3-BORONIC ACID 2-Methyl-3-pyridineboronic acid 2-methylpyridine-3-boronic acid 2-Methylpyridin-3-ylboronic acid 2-METHYL-3-PYRIDINYLBORONIC ACID Boronic acid, B-(2-Methyl-3-pyridinyl)- |
CAS | 899436-71-6 |
InChI | InChI=1/C6H8BNO2/c1-5-6(7(9)10)3-2-4-8-5/h2-4,9-10H,1H3 |
Molecular Formula | C6H8BNO2 |
Molar Mass | 136.94 |
Density | 1.18±0.1 g/cm3(Predicted) |
Boling Point | 303.6±44.0 °C(Predicted) |
pKa | 4.08±0.58(Predicted) |
Storage Condition | Inert atmosphere,Store in freezer, under -20°C |
Refractive Index | 1.527 |
Risk Codes | R22 - Harmful if swallowed R41 - Risk of serious damage to eyes R37/38 - Irritating to respiratory system and skin. |
Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S39 - Wear eye / face protection. |
Hazard Class | IRRITANT |
Application | 2-methylpyridine-3-boronic acid is an organic intermediate, it can be prepared from 3-bromo-2-methylpyridine and triisopropyl borate in one step. 2-methylpyridine-3-boronic acid can be used to participate in the Suzuki reaction. |
preparation | to 3-bromo-2-methylpyridine (4.00g,23 mmol) at -78°C butyl lithium (17mL,28 mmol) was added dropwise to a solution of triisopropyl borate (6.40 mL,28 mmol) and 50 mL/1 toluene/THF(4/1,50 mL). The mixture was heated to -70 °c over 30 minutes and then to 20 °c. HCl(2m) was added to bring the solution to pH 1. Water (20ml) was then added and the mixture was extracted with toluene. The aqueous layer was neutralized with 1M NaOH and extracted with dichloromethane. The aqueous layer was concentrated to dryness and the white solid was washed with dichloromethane. The combined organic layers were dried over sodium sulfate, filtered and concentrated to give 2.10g of 2-methylpyridine-3-boronic acid as a yellow oil. ES = 138.2(M H). |