5-Bromo-2-ethoxypyridine Chemical Properties

Melting point:

32-36 °C (lit.)

Boiling point:

107°C/33mmHg(lit.)

Density 

1.449±0.06 g/cm3(Predicted)

Flash point:

218 °F

storage temp. 

Inert atmosphere,Room Temperature

solubility 

soluble in Methanol

form 

Solid

pka

1.68±0.22(Predicted)

color 

Off-white to pale yellow

InChI

InChI=1S/C7H8BrNO/c1-2-10-7-4-3-6(8)5-9-7/h3-5H,2H2,1H3

InChIKey

WQXZKMUZWPUZGL-UHFFFAOYSA-N

SMILES

C1(OCC)=NC=C(Br)C=C1

CAS DataBase Reference

55849-30-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-37/38-41

Safety Statements 

26-36/39

WGK Germany 

3

Hazard Note 

Harmful

HazardClass 

IRRITANT

HS Code 

29333990

MSDS

• Language:English Provider:SigmaAldrich

5-Bromo-2-ethoxypyridine Usage And Synthesis

Chemical Properties

Light yellow Cryst

Synthesis

The general procedure for the synthesis of 5-bromo-2-ethoxypyridine from 2,5-dibromopyridine and ethanol was as follows: freshly cut sodium metal (74 mg, 3.2 mmol) was dissolved in anhydrous ethanol (1.2 mL), followed by the addition of a solution of 2,5-dibromopyridine (236 mg, 1 mmol) in dimethylformamide (DMF, 3 mL). The reaction mixture was stirred at 80 °C for 1 h and subsequently cooled to room temperature. Upon completion of the reaction, the reaction was quenched with deionized water (4 mL) and extracted three times with ether. The organic phases were combined, washed with saturated saline, dried over anhydrous sodium sulfate and subsequently concentrated under reduced pressure. Purification of the residue by fast column chromatography afforded the target product 5-bromo-2-ethoxypyridine as a white solid (192 mg, 95% yield). Mass spectrometry (MS) analysis showed (M+H)+ peaks at m/z 202 and 204.

References

[1] Patent: WO2009/155527, 2009, A2. Location in patent: Page/Page column 127
[2] Recueil des Travaux Chimiques des Pays-Bas, 1949, vol. 68, p. 275,282

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