2-CHLORO-4-ETHOXYPYRIDINE

2-CHLORO-4-ETHOXYPYRIDINE Property

Melting point:

55-57 °C

Boiling point:

230.9±20.0 °C(Predicted)

Density 

1.166±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

pka

2.25±0.10(Predicted)

Appearance

White to off-white Solid

Safety

HS Code 

2933399990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

2-CHLORO-4-ETHOXYPYRIDINE Chemical Properties,Usage,Production

Uses

2-Chloro-4-ethoxypyridine is a useful research chemical.

Synthesis

GENERAL STEPS: A solution of 2-chloro-4-nitropyridine (170 g, 1070 mmol) in THF (2 L) was slowly added to sodium ethoxide (109.45 g, 1610 mmol) at 0 °C. The reaction mixture was stirred at 25°C for 12 hours. The completion of the reaction was monitored by LCMS and TLC (unfolding agent: petroleum ether/ethyl acetate = 5:1, Rf = 0.6). After completion of the reaction, the mixture was filtered and the filtrate was concentrated under reduced pressure to remove most of the solvent. The residue was extracted with ethyl acetate (800 mL x 3), the organic layer was washed with saturated sodium chloride solution (1 L), dried over anhydrous sodium sulfate, and concentrated to give 2-chloro-4-ethoxypyridine (157 g, 1.0 mol, 92% yield) as a solid.1H NMR (400 MHz, CD3OD) δ 8.15 (d, J=6.0 Hz, 1H), 6.99 (d , J=2.0Hz, 1H), 6.91-6.89 (m, 1H), 4.16-4.14 (m, 2H), 1.41-1.38 (m, 3H). es-lcms m/z 158 ([M+H]+).

References

[1] Patent: WO2016/37578, 2016, A1. Location in patent: Page/Page column 71; 72
[2] Patent: WO2016/38519, 2016, A1. Location in patent: Page/Page column 34; 35
[3] Patent: WO2016/38552, 2016, A1. Location in patent: Page/Page column 49
[4] Patent: WO2014/141187, 2014, A1. Location in patent: Page/Page column 112; 52; 53
[5] ACS Medicinal Chemistry Letters, 2018, vol. 9, # 7, p. 623 - 628