4-Bromopyridine-2-carboxylic acid Chemical Properties

Melting point:

172-174

Boiling point:

347.8±27.0 °C(Predicted)

Density 

1.813±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Sparingly Soluble in DMSO, Methanol, Water

pka

3.25±0.10(Predicted)

form 

Solid

color 

Off-White

Water Solubility 

Sparingly soluble in dimethyl sulfoxide , methanol and water.

InChI

InChI=1S/C6H4BrNO2/c7-4-1-2-8-5(3-4)6(9)10/h1-3H,(H,9,10)

InChIKey

RPHHYRNGCJYQSP-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

30766-03-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

20/21/22

Safety Statements 

24/25-36/37

HazardClass 

IRRITANT

HS Code 

29339900

4-Bromopyridine-2-carboxylic acid Usage And Synthesis

Chemical Properties

4-Bromopyridine-2-carboxylic acid is fine needles

Uses

4-Bromopyridine-2-carboxylic acid is a useful synthetic intermediate

Uses

4-Bromopicolinic acid is a useful synthetic intermediate. Also used as a intermediate for agrochemical, pharmaceutical and dyestuff field.

Synthesis

4.1.12 Synthesis of 5-bromopyridine-2-carboxylic acid (16): In a 250 mL three-necked flask equipped with a stirrer, thermometer, and condenser tube, 100 mL of water and 4-bromo-2-methylpyridine (15) (4.0 g, 23 mmol) were added. After the mixture was stirred and heated to 80 °C, potassium permanganate (KMnO4) (16.6 g, 105 mmol) was added in three batches at 1 h intervals. The reaction mixture was kept stirred at 80 °C for 3-4 hours. After completion of the reaction, the clarified filtrate was obtained by filtration. The pH of the filtrate was adjusted to 4-5 with concentrated hydrochloric acid (HCl), at which time a small amount of white solid was precipitated, which was a small amount of product (16). After filtration, the filtrate was concentrated in vacuum. To the concentrated residue, an appropriate amount of ethanol was added to dissolve the compound (16), at which time a large amount of white solid precipitated, which was removed by filtration. Finally, the filtrate was concentrated in vacuum to give a light yellow solid product (16) (1.70 g, 33% yield).

References

[1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 13, p. 3228 - 3236
[2] Patent: WO2008/57497, 2008, A2. Location in patent: Page/Page column 292-293
[3] Patent: WO2007/89669, 2007, A2. Location in patent: Page/Page column 204
[4] Patent: WO2008/57469, 2008, A1. Location in patent: Page/Page column 292-293
[5] Patent: WO2008/57468, 2008, A1. Location in patent: Page/Page column 292-293

4-Bromopyridine-2-carboxylic acid(30766-03-1)Related Product Information

• 2,5-PYRIDINEDICARBOXYLIC ACID
• 4-Bromopyridine
• 2,6-Lutidine
• 1-Hexadecylpyridinium bromide
• Chromium picolinate
• 2-Picolinic acid
• 2-Chloro-3-cyanopyridine
• Quinolinic acid
• 5-Bromopicolinic acid
• 6-BROMOPYRIDINE-2-CARBOXYLIC ACID
• 4-BROMO-PYRIDINE-2-CARBOXYLIC ACID METHYL ESTER
• 4-BROMOPYRIDINE-2,6-DICARBOXYLIC ACID
• 4-Bromo-pyridine-2-carboxylic acid ethyl ester
• 3-BROMOPYRIDINE-4-CARBOXYLIC ACID
• 2,6-Dibromopyridine-4-carboxylic acid
• 5-BROMOPYRIDINE-2-CARBOXYLIC ACID METHYL ESTER
• 2-BROMOPYRIDINE-3-CARBOXYLIC ACID
• 6-BROMOPYRIDINE-3-CARBOXYLIC ACID,2-BROMOPYRIDINE-5-CARBOXYLIC ACID