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2-Methoxy-4-methylpyridine

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Products Intro: Product Name:2-methoxy-4-methylpyridine
CAS:100848-70-2
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Products Intro: Product Name:2-Methoxy-4-methylpyridine
CAS:100848-70-2
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2-Methoxy-4-methylpyridine Basic information
Product Name:2-Methoxy-4-methylpyridine
Synonyms:2-METHOXY-4-PICOLINE;2-METHOXY-4-METHYLPYRIDINE;Pyridine, 2-methoxy-4-methyl- (9CI);2-METHOXY-4-METHYLPYRIDINEV;2-METHOXY-4-PICOLINE (2-METHOXY-4-METHYLPYRIDINE);Pyridine, 2-methoxy-4-methyl-;2-Methoxy-p-picoline;2-Methoxy-4-Methylpyridine,97%
CAS:100848-70-2
MF:C7H9NO
MW:123.15
EINECS:
Product Categories:C7 and C8;Heterocyclic Building Blocks;Pyridines;PYRIDINE;Pyrroles ,Pyrimidines
Mol File:100848-70-2.mol
2-Methoxy-4-methylpyridine Structure
2-Methoxy-4-methylpyridine Chemical Properties
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
pka4.07±0.10(Predicted)
form clear liquid
color Colorless to Almost colorless
CAS DataBase Reference100848-70-2(CAS DataBase Reference)
Safety Information
Hazard Codes Xi
Risk Statements 10-36/37/38
Safety Statements 16-26-36
RIDADR UN 1993 3/PG 3
WGK Germany 3
Hazard Note Irritant
HazardClass 3
PackingGroup 
HS Code 29339900
MSDS Information
ProviderLanguage
SigmaAldrich English
2-Methoxy-4-methylpyridine Usage And Synthesis
Description2-Methoxy-4-methylpyridine is an organic intermediate, which can be prepared by nucleophilic substitution of 2-chloro-4-methylpyridine with sodium methoxide.
Uses2-Methoxy-4-methylpyridine is a heterocyclic organic compound and can be used as an organic intermediate.
PreparationThe mixture of 2-chloro-4-picoline and NaOCH3 in DMSO was extracted with ethyl acetate and reacted to obtain 2-methoxy-4-picoline.
Synthesis
2-Hydroxy-4-methylpyridine

13466-41-6

Iodomethane

74-88-4

2-Methoxy-4-methylpyridine

100848-70-2

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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