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

Flash point:

53 °C

storage temp. 

Inert atmosphere,Room Temperature

pka

4.07±0.10(Predicted)

form 

clear liquid

color 

Colorless to Almost colorless

CAS DataBase Reference

100848-70-2(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 

Ⅲ

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich

2-Methoxy-4-methylpyridine Usage And Synthesis

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

2-Methoxy-4-methylpyridine(100848-70-2)Related Product Information

• 2-Methoxy-5-methylpyridine
• 2-METHOXY-6-METHYLPYRIDINE
• Chromium picolinate
• Azamethiphos
• 2,6-Lutidine
• 2-Methoxypyridine
• 2-Chloro-5-chloromethylpyridine
• 4-Methylpyridine
• 2,4,6-Collidine
• 2-Methyl-4-methoxybenzenamine
• 2-Picoline
• 4-Methoxypyridine
• 4-Amino-2-methoxypyridine
• 3-BROMO-6-METHOXY-2-METHYLPYRIDINE,5-Bromo-2-Methoxy-6-Methylpyridine
• 2-METHOXY-5-NITRO-6-PICOLINE
• 4-CHLORO-2-METHOXY-PYRIDINE
• 2-Methoxy-5-(trifluoromethyl)pyridine
• 5-Chloro-2-methoxypyridine