5-Bromo-3-Methoxy-Pyridine2-Carbonitrile

5-Bromo-3-Methoxy-Pyridine2-Carbonitrile Property

Boiling point:

310.9±37.0 °C(Predicted)

Density 

1.65±0.1 g/cm3(Predicted)

storage temp. 

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

form 

solid

pka

-7.15±0.10(Predicted)

Appearance

White to yellow Solid

InChI

InChI=1S/C7H5BrN2O/c1-11-7-2-5(8)4-10-6(7)3-9/h2,4H,1H3

InChIKey

WIRVBLLSXJUOHZ-UHFFFAOYSA-N

SMILES

C1(C#N)=NC=C(Br)C=C1OC

Safety

Hazard Codes 

T

Risk Statements 

25

Safety Statements 

45

RIDADR 

UN 2811 6.1 / PGIII

WGK Germany 

3

HazardClass 

IRRITANT

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H301Toxic if swalloed

Precautionary statements

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

5-Bromo-3-Methoxy-Pyridine2-Carbonitrile Chemical Properties,Usage,Production

Synthesis

Sodium methanolate (2.68 g, 49.59 mmol) was added to a solution of 5-bromo-3-fluoropyridine-2-carbonitrile (2.00 g, 9.93 mmol) in tetrahydrofuran (THF, 80 mL) at room temperature. The reaction mixture was stirred at 70 °C for 3 hours. Upon completion of the reaction, the pH of the reaction mixture was adjusted to 7 with a 3 M solution of HCl. The reaction mixture was extracted with ethyl acetate (100 mL x 3). The organic phases were combined, washed with brine and dried over anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure to give 5-bromo-3-methoxypyridine-2-carbonitrile as a brown solid (2.00 g, 95% yield). Mass spectrum (MS): m/z = 213.0 [M + H]+.

References

[1] Patent: US2016/376283, 2016, A1. Location in patent: Paragraph 1219; 1220
[2] Patent: EP3275864, 2018, A1. Location in patent: Paragraph 0032; 0038; 0044; 0050; 0056; 0062
[3] Patent: WO2007/87488, 2007, A2. Location in patent: Page/Page column 24