| Company Name: |
Anichem Inc. |
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0512-69369885 |
| Email: |
sales@anichem.com.cn |
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| | 5-FORMYL-2-METHOXY-4-PICOLINE Basic information |
| Product Name: | 5-FORMYL-2-METHOXY-4-PICOLINE | | Synonyms: | 5-FORMYL-2-METHOXY-4-PICOLINE;3-Pyridinecarboxaldehyde, 6-methoxy-4-methyl- (9CI);6-methoxy-4-methylnicotinaldehyde;6-Methoxy-4-methyl-3-pyridinecarboxaldehyde;CML-015;3-Pyridinecarboxaldehyde, 6-methoxy-4-methyl-;2-Fluoro-37-(methylthio)pyridine | | CAS: | 123506-66-1 | | MF: | C8H9NO2 | | MW: | 151.16 | | EINECS: | | | Product Categories: | ALDEHYDE;Pyridine | | Mol File: | 123506-66-1.mol |  |
| | 5-FORMYL-2-METHOXY-4-PICOLINE Chemical Properties |
| Melting point | 91-92 °C(Solv: hexane (110-54-3)) | | Boiling point | 274.2±35.0 °C(Predicted) | | density | 1.123±0.06 g/cm3(Predicted) | | storage temp. | under inert gas (nitrogen or Argon) at 2-8°C | | pka | 2.25±0.18(Predicted) | | Appearance | White to off-white Solid |
| | 5-FORMYL-2-METHOXY-4-PICOLINE Usage And Synthesis |
| Synthesis | General procedure for the synthesis of 5-formyl-2-methoxy-4-methyl-4-methylpyridine from 2-methoxy-4-methyl-5-bromopyridine and N,N-dimethylformamide: 5-bromo-2-methoxy-4-methylpyridine (2.6 g, 13 mmol) was dissolved in anhydrous THF (40 mL) and cooled to -70 °C under argon protection. A hexane solution of 1.6 M n-butyllithium (8.1 mL, 14 mmol) was slowly added over 10 min with stirring. The reaction temperature was maintained at -70 °C and stirring was continued for 30 min. Subsequently, anhydrous DMF (1.2 mL, 15 mmol) was added in batches, keeping the temperature constant. After addition, stirring was continued at -70 °C for 30 min, then brought to room temperature and stirred overnight. Upon completion of the reaction, the reaction was quenched with 1 M hydrochloric acid (40 mL) and subsequently extracted three times with tert-butyl methyl ether (TBME). The organic phases were combined, washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. Purification by column chromatography using tert-butyl methyl ether-light petroleum ether (1:1) as eluent afforded 1.8 g (91% yield) of 5-formyl-2-methoxy-4-methylpyridine as a light yellow solid.LC-MS m/z 152 (M + 1); 1H NMR (CDCl3) δ 10.1 (s, 1H), 8.55 (s, 1H), 6.61 ( s, 1H), 4.05 (s, 3H), 2.60 (s, 3H) ppm. | | References | [1] Patent: WO2006/65215, 2006, A1. Location in patent: Page/Page column 19; 35
[2] Synthetic Communications, 2009, vol. 39, # 17, p. 3060 - 3068
[3] Patent: WO2015/158427, 2015, A1. Location in patent: Page/Page column 84; 85 |
| | 5-FORMYL-2-METHOXY-4-PICOLINE Preparation Products And Raw materials |
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