5-Bromo-6-methoxypyridine-2-carboxylic acid Chemical Properties

Boiling point:

323.8±42.0 °C(Predicted)

Density 

1.713±0.06 g/cm3(Predicted)

storage temp. 

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

form 

solid

pka

3.29±0.10(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C7H6BrNO3/c1-12-6-4(8)2-3-5(9-6)7(10)11/h2-3H,1H3,(H,10,11)

InChIKey

AIHBRPSPSCCVPH-UHFFFAOYSA-N

SMILES

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

Safety Information

RIDADR 

UN2811

5-Bromo-6-methoxypyridine-2-carboxylic acid Usage And Synthesis

Synthesis

Synthesis of 5-bromo-6-methoxypyridinecarboxylic acid: 5-bromo-6-chloropyridinecarboxylic acid (15.0 g, 63.4 mmol, 1.0 eq.) was suspended in methanol (130 mL) at room temperature, to which was added 4.37 M methanolic solution of sodium methanolate (58.0 mL, 253 mmol, 4.0 eq.). The reaction mixture was heated at 80 °C for 18 hours to form a thick mixture. Subsequently, the reaction mixture was diluted with methanol (100 mL) and stirring was continued at 80 °C for 24 hours. After completion of the reaction, the mixture was cooled to room temperature, acidified to pH=3 with concentrated aqueous hydrochloric acid, diluted with water and extracted with ethyl acetate (three times). The organic layers were combined, dried with magnesium sulfate, filtered and concentrated to give a residue. The residue was co-evaporated with dichloromethane/hexane (1:1 mixture, 200 mL, three times) to give the final 5-bromo-6-methoxypyridine carboxylic acid (13.9 g, 94% yield) as a white solid.1H NMR (500 MHz, CDCl3) δ 10.22 (br s, 1H), 8.06 (d, J = 7.7 Hz, 1H), 7.73 (d, J = 7.7 Hz, 1H), 4.10 (s, 3H).LCMS (ES-) [M-H]-: 229.9/231.9.

References

[1] Patent: WO2016/201168, 2016, A1. Location in patent: Paragraph 0174

5-Bromo-6-methoxypyridine-2-carboxylic acid(1214334-70-9)Related Product Information

• 2-Pyridinecarboxylic acid, 5-bromo-6-fluoro-, methyl ester
• Methyl 5-broMo-6-Methoxypicolinate
• 5-BROMO-6-METHOXYPYRIDIN-2-AMINE
• 3-PYRIDINECARBONITRILE, 5-BROMO-6-METHOXY-
• METHYL 6-AMINO-5-BROMONICOTINATE
• 5-BroMo-6-Methoxy-nicotinic acid
• 5-Bromo-6-methoxynicotinic acid methyl ester
• Chromium picolinate