5-CHLORO-3-TRIFLUOROMETHYL-1H-PYRAZOLE

5-CHLORO-3-TRIFLUOROMETHYL-1H-PYRAZOLE Property

Boiling point:

214.4±35.0 °C(Predicted)

Density 

1.602±0.06 g/cm3(Predicted)

storage temp. 

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

pka

7.60±0.10(Predicted)

Appearance

White to off-white Solid

Safety

HS Code 

2933199090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

5-CHLORO-3-TRIFLUOROMETHYL-1H-PYRAZOLE Chemical Properties,Usage,Production

Synthesis

The general procedure for the synthesis of 5-chloro-N,N-dimethyl-3-(trifluoromethyl)-1H-pyrazole-1-sulfonamide from 5-chloro-N,N-dimethyl-3-(trifluoromethyl)-1H-pyrazole is as follows: 5-chloro-N,N-dimethyl-3-(trifluoromethyl)-1H-pyrazole-1-sulfonamide (8.0 g, 29 mmol) was dissolved in a reaction system at 0°C with trifluoroacetic acid (TFA, 11 mL. 140 mmol) were co-dissolved in the reaction system. Subsequently, the reaction mixture was stirred continuously at room temperature overnight. Upon completion of the reaction, the solvent was removed by concentration under reduced pressure and the resulting residue was diluted with ethyl acetate (EtOAc, 50 mL) and washed with water (50 mL). The aqueous layer was further extracted with ethyl acetate (2 x 50 mL). All organic phases were combined, dried with anhydrous sodium sulfate (Na2SO4), filtered into a round bottom flask and finally concentrated under reduced pressure to afford the target product 5-chloro-3-trifluoromethyl-1H-pyrazole (5.0 g, 29 mmol, 100% yield). The structure of the product was confirmed by 1H NMR (400 MHz, DMSO-d6) with chemical shift δppm 6.97 (s, 1H).

References

[1] Patent: WO2014/152738, 2014, A1. Location in patent: Page/Page column 67
[2] Patent: WO2015/52226, 2015, A1. Location in patent: Paragraph 0452
[3] Patent: WO2008/91594, 2008, A2. Location in patent: Page/Page column 90
[4] Patent: US2010/240619, 2010, A1. Location in patent: Page/Page column 64
[5] Journal of Medicinal Chemistry, 2016, vol. 59, # 6, p. 2760 - 2779