5-Chloro-2-methoxypyridine Chemical Properties

Boiling point:

181-182 °C (lit.)

Density 

1.193 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.5260(lit.)

Flash point:

128 °F

storage temp. 

Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to lump

pka

1.12±0.10(Predicted)

Specific Gravity

1.193

color 

White to Almost white

CAS DataBase Reference

13473-01-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

10-22-41-36/37/38

Safety Statements 

26-39-37/39

RIDADR 

UN 1993 3/PG 3

WGK Germany 

3

HazardClass 

3

PackingGroup 

III

HS Code 

29333990

MSDS

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5-Chloro-2-methoxypyridine Usage And Synthesis

Chemical Properties

Colorless to light yellow liquid

Uses

Reactant for:

• Preparation of biaryls via palladium-catalyzed Hiyama cross-coupling with aryltrifluorosilanes
• Suzuki-Miyaura cross-coupling reactions

Synthesis

1. Sodium hydride (60% dispersed in mineral oil, 5.50 g, 115 mmol, 2 eq.) was added in batches to dry methanol (distilled after treatment with magnesium strips, 25 mL) under nitrogen protection. 2. 2,5-Dichloropyridine (10.0 g, 68 mmol) was added to the above solution. 3. The reaction mixture was refluxed for 18 hours. 4. After completion of the reaction, the reaction was cooled to room temperature and treated with an excess of solid potassium bicarbonate. 5. and treated with excess solid potassium bicarbonate.5. The reaction mixture was filtered and the filtrate was concentrated to 50% of the original volume, at which point solids precipitated out of the solution.6. The solids were washed with hexane, and the washings were combined and concentrated to give the oily material.7. 2-methoxy-5-chloropyridine was purified by distillation under reduced pressure (102 °C, 2400 Pascals) to give 6.30 g (65% yield) as a colorless oily material. colorless oil. Mass spectra (chemical ionization, CH4) m/z: 144 (M+, 100), 146 (44), 172 (M+28, 19), 124 (9).

References

[1] Journal of the Chemical Society, Perkin Transactions 1, 2000, # 8, p. 1245 - 1249
[2] Patent: US5512575, 1996, A

5-Chloro-2-methoxypyridine(13473-01-3)Related Product Information

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