5-Bromo-6-chloronicotinic acid Chemical Properties

Melting point:

166-168°C

Boiling point:

370.0±42.0 °C(Predicted)

Density 

1.917±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

2.85±0.10(Predicted)

color 

White to Light yellow

InChI

InChI=1S/C6H3BrClNO2/c7-4-1-3(6(10)11)2-9-5(4)8/h1-2H,(H,10,11)

InChIKey

DXEUARPQHJXMII-UHFFFAOYSA-N

SMILES

C1=NC(Cl)=C(Br)C=C1C(O)=O

CAS DataBase Reference

29241-62-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22-36/37/38

Safety Statements 

26-36/37/38

HazardClass 

IRRITANT

HS Code 

29333990

5-Bromo-6-chloronicotinic acid Usage And Synthesis

Chemical Properties

White solid

Uses

5-Bromo-6-chloronicotinic acid is a biochemical reagent that can be used as a biological material or organic compound for life science related research.

Synthesis

Synthesis of 5-bromo-6-chloronicotinic acid: 5-bromo-6-hydroxynicotinic acid (10 g, 45 mmol), tetramethylammonium chloride (5.4 g, 49 mmol), and phosphorus triclosan (20 mL) were sequentially added to a reaction flask, and the mixture was heated to reflux and held for 3 hours. Upon completion of the reaction, the reaction mixture was slowly poured into ice water and stirred continuously for 2 hours. The precipitated solid was collected by filtration, dissolved in ethyl acetate (300 mL) and dried by adding anhydrous sodium sulfate. The desiccant was removed by filtration and the filtrate was concentrated under reduced pressure to give 10.5 g (97% yield) of the target product 5-bromo-6-chloronicotinic acid as a pink solid. The product was characterized by 1H NMR (400 MHz, DMSO-d6): δ 8.53 (d, J = 2.02 Hz, 1H), 8.85 (d, J = 2.02 Hz, 1H), 13.57 (s, 1H).

References

[1] Patent: WO2007/70818, 2007, A1. Location in patent: Page/Page column 103
[2] Journal of Medicinal Chemistry, 2005, vol. 48, # 15, p. 4892 - 4909
[3] Journal of Medicinal Chemistry, 2013, vol. 56, # 24, p. 9874 - 9896

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