2-BROMO-5-METHOXYPYRIDINE Chemical Properties

Melting point:

22 °C

Boiling point:

113 °C(Press: 59 Torr)

Density 

1.530±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

soluble in Methanol

form 

powder to lump

pka

-2.22±0.10(Predicted)

color 

White to Almost white

InChI

InChI=1S/C6H6BrNO/c1-9-5-2-3-6(7)8-4-5/h2-4H,1H3

InChIKey

WULVUFYZVYHTFX-UHFFFAOYSA-N

SMILES

C1(Br)=NC=C(OC)C=C1

CAS DataBase Reference

105170-27-2

Safety Information

Hazard Codes 

Xi

Hazard Note 

Irritant

HS Code 

2933399990

2-BROMO-5-METHOXYPYRIDINE Usage And Synthesis

Chemical Properties

Pale yellow liquid

Uses

2-Bromo-5-methoxypyridine is a reagent used in preparation of tetrahydroisoquinoline amides as bronchodilators.

Synthesis

General procedure for the synthesis of 2-bromo-5-methoxypyridine from 2-amino-5-methoxypyridine: (a) 2-Amino-5-methoxypyridine (14.8 g, prepared according to the method described by JG Lombardino, J. Med. Chem., 1981, 24, 39) was dissolved in 60% hydrobromic acid (150 ml) and cooled to -10°C. Bromine (47.47 g) was added slowly and dropwise with stirring. A solution of sodium nitrite (20.53 g) in water (40 ml) was added dropwise to the resulting yellow suspension, keeping the reaction temperature below -5°C. The mixture was stirred to room temperature and cooled to 0°C after 0.5 h. A solution of sodium hydroxide (120 g) in water (100 ml) was added slowly. The mixture was fully extracted with ether, the ether extracts were combined and dried with anhydrous sodium sulfate, followed by evaporation of the solvent. The residue was purified by column chromatography on silica gel (150 g), using dichloromethane as eluent to give a yellow oil (14.1 g, 63% yield). This product was combined with a smaller batch (3.4 g) and purified by distillation under reduced pressure to give finally 2-bromo-5-methoxypyridine (16.4 g) with a boiling point of 76°C-78°C/0.6 torr.

References

[1] Pharmazie, 2000, vol. 55, # 12, p. 907 - 912
[2] Patent: US4766121, 1988, A
[3] Patent: EP188351, 1991, B1
[4] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1988, p. 3085 - 3096

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