2,6-Dibromopyridine-4-carboxylic acid Chemical Properties

Melting point:

184-185 °C(Solv: water (7732-18-5))

Boiling point:

487.5±45.0 °C(Predicted)

Density 

2.202±0.06 g/cm3(Predicted)

storage temp. 

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

form 

solid

pka

2.59±0.10(Predicted)

color 

White to off white

InChI

InChI=1S/C6H3Br2NO2/c7-4-1-3(6(10)11)2-5(8)9-4/h1-2H,(H,10,11)

InChIKey

AULQTVXAKNKCCA-UHFFFAOYSA-N

SMILES

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

Safety Information

Hazard Codes 

Xi

HS Code 

2933399990

2,6-Dibromopyridine-4-carboxylic acid Usage And Synthesis

Chemical Properties

Pale yellow solid

Uses

2,?6-?Dibromopyridine-?4-?carboxylic Acid is an analog of 2,6-Dichloroisonicotinic acid which binds and inhibits tobacco catalase activity.

Synthesis

General procedure for the synthesis of 2,6-dibromopyridine-4-carboxylic acid from citrazinic acid: Citrazinic acid (2.33 g, 0.015 mol) was mixed with phosphorus tribromide and heated to 180 °C under nitrogen protection for 3 hours. After completion of the reaction, the reaction mixture was cooled and quenched carefully with ice water. The reaction mixture was filtered and the aqueous phase was extracted with dichloromethane (4 x 40 ml). The solid fraction was continuously extracted in a Soxhlet extractor using dichloromethane for 12 hours. The directly extracted organic phase was dried with anhydrous sodium sulfate, filtered and concentrated to give 2.2 g of slightly red solid. The organic phase of Soxhlet extraction was similarly dried with anhydrous sodium sulfate, filtered and concentrated to give 0.5 g of a slightly red solid. The two fractions of 2,6-dibromoisonicotinic acid (64% total yield) were combined after confirmation of structural identity by NMR hydrogen spectroscopy (CDCl3, δ 8.04, 2H, s).

References

[1] Journal of Medicinal Chemistry, 2013, vol. 56, # 12, p. 5079 - 5093
[2] Tetrahedron, 2007, vol. 63, # 2, p. 291 - 298
[3] Organic and Biomolecular Chemistry, 2005, vol. 3, # 8, p. 1460 - 1467
[4] Patent: WO2005/84439, 2005, A1. Location in patent: Page/Page column 35
[5] Synthesis, 2000, # 8, p. 1138 - 1142

2,6-Dibromopyridine-4-carboxylic acid(2016-99-1)Related Product Information

• 1,3-Dibromo-5,5-dimethylhydantoin
• 2,2-Bis(bromomethyl)propane-1,3-diol
• Chromium picolinate
• 2,6-Lutidine
• 2,4-DIBROMOBIPHENYL
• 2,5-PYRIDINEDICARBOXYLIC ACID
• 3,5-Dibromopyridine
• Isonicotinic acid
• Quinolinic acid
• 2,6-Dibromopyridine
• 1,2-Dibromopropane
• 2,6-Dichloroisonicotinic acid
• 2,6-DIBROMO-3,5-DIFLUOROISONICOTINIC ACID
• 5,6-DIBROMOPYRIDINE-3-CARBOXYLIC ACID
• Methyl 2,6-dibromopyridine-4-carboxylate
• Ethyl 2,6-dibromopyridine-4-carboxylate
• 2,6-Dibromopyridine-4-carboxylic acid
• CARBOXYLIC ACID