| Identification | Back Directory | [Name]
6-Bromo-3-hydroxy-2-methylpyridine | [CAS]
118399-86-3 | [Synonyms]
CML-033
6-Bromo-2-methylpyridin-3-o
6-broMo-2-Methylpyridin-3-ol
6-bromo-2-methyl-3-Pyridinol
3-Pyridinol, 6-bromo-2-methyl-
6-Bromo-3-hydoxy-2-methylpyridine
6-Bromo-3-hydroxy-2-methylpyridine | [Molecular Formula]
C6H6BrNO | [MDL Number]
MFCD11044277 | [MOL File]
118399-86-3.mol | [Molecular Weight]
188.02 |
| Chemical Properties | Back Directory | [Melting point ]
201-203.5℃ | [Boiling point ]
346.2±37.0 °C(Predicted) | [density ]
1.655±0.06 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,2-8°C | [pka]
9.92±0.10(Predicted) | [Appearance]
White to off-white Solid |
| Hazard Information | Back Directory | [Synthesis]
Step 2: Synthesis of 6-bromo-2-methylpyridin-3-ol
4,6-Dibromo-2-methylpyridin-3-ol (15.8 g, 59.4 mmol) was dissolved in tetrahydrofuran (THF, 200 mL). The reaction solution was cooled to -78°C and n-butyllithium (n-BuLi, 50 mL, 125 mmol, 2.5 M hexane solution) was slowly added dropwise at this temperature. After the dropwise addition, the reaction temperature was maintained at -78°C and stirring was continued for 2 hours. Upon completion of the reaction, the reaction was quenched with deionized water (50 mL) and the reaction solution was neutralized with 2 N hydrochloric acid (HCl). Subsequently, the aqueous phase was extracted with dichloromethane (2 x 50 mL). The organic phases were combined, dried with anhydrous sodium sulfate (Na2SO4) and concentrated under reduced pressure to afford 6-bromo-2-methylpyridin-3-ol (10.5 g, 95% yield) as a yellow oil. The product was confirmed by nuclear magnetic resonance hydrogen spectroscopy (1H NMR, 300 MHz, DMSO-d6): δ 2.29 (s, 3H), 7.08 (d, 1H), 7.26 (d, 1H), 10.08 (s, 1H). | [References]
[1] Patent: WO2012/112743, 2012, A1. Location in patent: Page/Page column 153-154
[2] Patent: WO2012/125613, 2012, A1. Location in patent: Page/Page column 139
[3] Patent: US2012/196869, 2012, A1. Location in patent: Paragraph 0338; 0339
[4] Patent: WO2013/109521, 2013, A1. Location in patent: Paragraph 00261; 00262
[5] Synlett, 2003, # 11, p. 1678 - 1682 |
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Tetranov Biopharm
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SynAsst Chemical.
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Cool Pharm, Ltd
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