6-Bromonicotinic acid Chemical Properties

Melting point:

200-203 °C(lit.)

Boiling point:

343.3±27.0 °C(Predicted)

Density 

1.813±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

pka

3.24±0.10(Predicted)

form 

Crystalline Powder

color 

White

InChI

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

InChIKey

JDJBRMNTXORYEN-UHFFFAOYSA-N

SMILES

C1=NC(Br)=CC=C1C(O)=O

CAS DataBase Reference

6311-35-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-36/37/38

Safety Statements 

26-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29333990

MSDS

• Language:English Provider:SigmaAldrich

6-Bromonicotinic acid Usage And Synthesis

Chemical Properties

Off-white Plates

Uses

A potential hypolipidemic agent; a nicotinic acid analog

Synthesis

General procedure for the synthesis of 6-bromonicotinic acid from 2-bromo-5-methylpyridine: 2-bromo-5-methylpyridine (100 g, 0.291 mol) was dissolved in 1000 mL of water and Aliquat 336 (2 mL) was added as a phase transfer catalyst. Subsequently, potassium permanganate (251 g, 0.797 mol) was added slowly over 1 hr. The reaction mixture was stirred at 110 °C for 30 min and continued for 1 h to ensure complete reaction. Upon completion of the reaction, the mixture was filtered through diatomaceous earth while hot and the diatomaceous earth was washed with hot water. The filtrate was concentrated to half the original volume under reduced pressure. To the concentrate was added 48% hydrobromic acid (about 300 mL), and the precipitated 6-bromonicotinic acid crystals were filtered, washed with water and dried to give 52 g of white crystals in 44% yield. The product was characterized by 1H-NMR (CDCl3) with chemical shift δ (ppm) of 7.64 (1H, d, J = 8.0 Hz), 8.08 (1H, d, J = 8.0 Hz), 9.03 (1H, s).

References

[1] Synthesis, 1994, # 1, p. 87 - 92
[2] Journal of Materials Chemistry, 2005, vol. 15, # 48, p. 5164 - 5173
[3] Patent: EP1391451, 2004, A1. Location in patent: Page 143
[4] Journal of Organic Chemistry, 1949, vol. 14, p. 509,513
[5] Synthesis, 2003, # 4, p. 551 - 554

6-Bromonicotinic acid(6311-35-9)Related Product Information

• 5-Bromonicotinic acid
• Ethyl 6-bromopicolinate
• N,N-Dimethylpropionamide
• 2,2-Dimethylbutyryl chloride
• 2-Phenylbutyric acid
• (6-BROMO-PYRIDIN-3-YL)-METHANOL
• 2-BROMO-5-METHOXYPYRIDINE
• 2-Bromo-5-methylpyridine
• 2-Bromo-6-(trifluoromethyl)pyridine
• 2-Bromo-6-methylpyridine
• 2-BROMO-5-IODOBENZYL ALCOHOL
• 2-Bromo-5-nitropyridine
• 2-Bromo-5-(trifluoromethyl)pyridine
• 5-Amino-2-bromopyridine
• 2-BROMO-5-METHOXYANILINE
• 2-Bromo-5-chloropyridine
• 2-Bromo-5-fluoropyridine
• 5-BROMONICOTINIC ACID 10-METHOXY-1,6-DIMETHYLERGOLINE-8-METHANOL ESTER,5-BROMONICOTINIC ACID 10-METHOXY-1,6-DIMETHYLERGOLINE-8-METHYL ESTER