3-BroMo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylic acid Chemical Properties

Melting point:

197-200 °C

Boiling point:

477.4±45.0 °C(Predicted)

Density 

1.92±0.1 g/cm3(Predicted)

vapor pressure 

0Pa at 20℃

storage temp. 

2-8°C

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

2.39±0.36(Predicted)

color 

White to Light Brown

Water Solubility 

8.84g/L at 20.3℃

InChI

InChI=1S/C9H5BrClN3O2/c10-7-4-6(9(15)16)14(13-7)8-5(11)2-1-3-12-8/h1-4H,(H,15,16)

InChIKey

FORBXGROTPOMEH-UHFFFAOYSA-N

SMILES

N1(C2=NC=CC=C2Cl)C(C(O)=O)=CC(Br)=N1

LogP

1.5 at 25℃

Safety Information

TSCA 

TSCA listed

HS Code 

2933199090

3-BroMo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylic acid Usage And Synthesis

Uses

3-Bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxylic acid is a useful building block and has been used in the synthesis of the pesticide Cyclaniliprole.

Flammability and Explosibility

Not classified

Synthesis

At -78 °C, 2-(3-bromo-1H-pyrazol-1-yl)-3-chloropyridine (3.04 g, 11.8 mmol) was dissolved in anhydrous THF (25 mL), keeping the reaction temperature below -71 °C. LDA solution (6 mL, 2M) was added slowly and dropwise. The reaction mixture was stirred at -78 °C for 15 min and then bubbled with carbon dioxide gas for 10 min. Subsequently, the reaction system was slowly warmed to -57°C and continued to -20°C. Upon completion of the reaction, the reaction was quenched with water. The reaction mixture was concentrated and dissolved in water (100 mL) and ether (80 mL), and an aqueous NaOH solution (1N, 2 mL) was added. The aqueous phase was washed with ether and acidified with aqueous HCl (2N). The precipitated solid was filtered, washed with water and dried to give 3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxylic acid (2 g, 59% yield) as a brown solid.

References

[1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 22, p. 6274 - 6279
[2] Patent: CN105669643, 2016, A. Location in patent: Paragraph 0072; 0075; 0076
[3] Patent: WO2006/68669, 2006, A1. Location in patent: Page/Page column 19; 25
[4] Patent: WO2003/106427, 2003, A2. Location in patent: Page 18-19
[5] Patent: WO2004/67528, 2004, A1. Location in patent: Page 27