| Identification | More | [Name]
2-Methoxy-4-methylpyridine | [CAS]
100848-70-2 | [Synonyms]
2-METHOXY-4-METHYLPYRIDINE
2-METHOXY-4-PICOLINE
Pyridine, 2-methoxy-4-methyl-(9CI)
2-METHOXY-4-METHYLPYRIDINEV
2-METHOXY-4-PICOLINE (2-METHOXY-4-METHYLPYRIDINE)
Pyridine, 2-methoxy-4-methyl- | [Molecular Formula]
C7H9NO | [MDL Number]
MFCD06200799 | [Molecular Weight]
123.15 | [MOL File]
100848-70-2.mol |
| Chemical Properties | Back Directory | [Melting point ]
136 °C | [Boiling point ]
152-153 °C (lit.) | [density ]
1.001±0.06 g/cm3(Predicted) | [refractive index ]
1.4990-1.5030 | [Fp ]
53 °C | [storage temp. ]
Inert atmosphere,Room Temperature | [form ]
clear liquid | [pka]
4.07±0.10(Predicted) | [color ]
Colorless to Almost colorless | [CAS DataBase Reference]
100848-70-2(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R10:Flammable.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S16:Keep away from sources of ignition-No smoking .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [RIDADR ]
UN 1993 3/PG 3
| [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HazardClass ]
3 | [PackingGroup ]
Ⅲ | [HS Code ]
29339900 |
| Hazard Information | Back Directory | [Description]
2-Methoxy-4-methylpyridine is an organic intermediate, which can be prepared by nucleophilic substitution of 2-chloro-4-methylpyridine with sodium methoxide. | [Uses]
2-Methoxy-4-methylpyridine is a heterocyclic organic compound and can be used as an organic intermediate. | [Preparation]
The mixture of 2-chloro-4-picoline and NaOCH3 in DMSO was extracted with ethyl acetate and reacted to obtain 2-methoxy-4-picoline. | [Synthesis]
To a stirred solution of 2-hydroxy-4-methylpyridine (10 g, 92 mmol) in chloroform (350 mL) was sequentially added silver carbonate (34.2 g, 124 mmol) and iodomethane (130 g, 920 mmol) at room temperature. The reaction mixture was stirred continuously under light-avoidance conditions for 48 hours. After completion of the reaction, the reaction mixture was filtered through diatomaceous earth and the filter cake was washed with ether. The filtrate was concentrated at a temperature below 20 °C and the resulting residue was purified by column chromatography using n-pentane/ether (5:1, v/v) as eluent to afford 2-methoxy-4-methylpyridine (8.0 g, 71% yield) as a colorless oil. The structure of the product was characterized by 1H NMR (CDCl3, δ): 8.02 (d, 1H, J=5.4 Hz), 6.69 (d, 1H, J=5.4 Hz), 6.55 (s, 1H), 3.91 (s, 3H), 2.28 (s, 3H); 13C NMR (CDCl3, δ): 164.40, 149.72, 146.31. 118.21, 110.88, 53.17, 20.81; Mass Spectrometry (MS) m/z (relative abundance): 123 (M+, 76%), 122 (100%) confirmed. | [References]
[1] Tetrahedron Letters, 1997, vol. 38, # 35, p. 6153 - 6156
[2] Patent: WO2005/806, 2005, A2. Location in patent: Page 72
[3] Journal of Medicinal Chemistry, 2003, vol. 46, # 6, p. 921 - 924 |
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