4-CHLORO-2-METHOXY-PYRIDINE Chemical Properties

Melting point:

26℃

Boiling point:

177℃

Density 

1.210

Flash point:

61℃

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly)

form 

Solid

pka

3.66±0.10(Predicted)

color 

White to Off-White

CAS DataBase Reference

72141-44-7(CAS DataBase Reference)

Safety Information

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

HS Code 

2933399990

4-CHLORO-2-METHOXY-PYRIDINE Usage And Synthesis

Uses

4-Chloro-2-methoxypyridine is a reagent in the preparation of cyclopalladated ferrocenylimines as efficient catalysts for the preparation of arylboronate esters.

Synthesis

General procedure for the synthesis of 4-chloro-2-methoxypyridine from 4-iodo-2-methoxypyridine: (d) 50.6 mL of isopropylmagnesium chloride (2 mol/L tetrahydrofuran solution) was mixed with 19.8 g (84.3 mmol) of the crude product of 4-iodo-2-methoxypyridine made in step (c) dissolved in 80 mL of tetrahydrofuran under ice bath cooling conditions. The reaction mixture was stirred at 0 °C for 1 hour, followed by continued stirring at room temperature for 1 hour. Then, 16.9 g (127 mmol) of N-chlorosuccinimide was slowly added and stirring was continued for 1 hour at room temperature. Upon completion of the reaction, the reaction was quenched by the addition of 100 mL of water and the tetrahydrofuran was removed by distillation under reduced pressure. The reaction mixture was extracted with ether and the organic layer was dried with sodium sulfate, filtered and the solvent was removed by decompression distillation to give 11.0 g (91% crude yield) of 4-chloro-2-methoxypyridine crude product. 1H-NMR (CDCl3, 400 MHz): δ (ppm) = 3.91 (s, 3H), 6.70 (d, 1H, J = 2.0 Hz), 6.81 (dd, 1H, J = 6.0 Hz, 2.0 Hz), 7.99 (d, 1H, J = 6.0 Hz).

References

[1] Patent: EP1559320, 2005, A1. Location in patent: Page/Page column 7

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