Methyl 2-amino-5-bromonicotinate Chemical Properties

Melting point:

143-146°C

Boiling point:

275.2±35.0 °C(Predicted)

Density 

1.662±0.06 g/cm3(Predicted)

storage temp. 

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

pka

2.45±0.49(Predicted)

Appearance

White to yellow Solid

InChI

InChI=1S/C7H7BrN2O2/c1-12-7(11)5-2-4(8)3-10-6(5)9/h2-3H,1H3,(H2,9,10)

InChIKey

POWKBBOOIZBIRZ-UHFFFAOYSA-N

SMILES

C1(N)=NC=C(Br)C=C1C(OC)=O

Safety Information

HazardClass 

IRRITANT

HS Code 

2933399990

Methyl 2-amino-5-bromonicotinate Usage And Synthesis

Uses

Methyl 2-Amino-5-bromonicotinate is a chemical reagent used in the synthesis of pharmaceutical agents.

Synthesis

To a stirred solution of methyl 2-aminopyridine-3-carboxylate (2 g, 13.15 mmol) and sodium bicarbonate (2.2 g, 26.31 mmol) in dichloromethane (30 mL) was slowly added a dichloromethane solution of bromine dropwise (1.01 mL bromine dissolved in 20 mL dichloromethane). The reaction mixture was stirred at room temperature for 1 hour. Upon completion of the reaction, the reaction was quenched with sodium bisulfite solution (50 mL). The reaction mixture was extracted with dichloromethane (2 x 40 mL) and the combined organic phases were washed with brine (40 mL) and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure to give methyl 2-amino-5-bromopyridine-3-carboxylate as a yellow solid (3 g, 99% yield).LCMS m/z (79Br/81Br) 231/233 (M+H)+.

References

[1] Patent: US2017/29420, 2017, A1. Location in patent: Paragraph 0034

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