4-(3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl)-phenylamine Chemical Properties

Melting point:

140-142 °C

Boiling point:

298.4±40.0 °C(Predicted)

Density 

1.52±0.1 g/cm3(Predicted)

storage temp. 

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

solubility 

DMSO : ≥ 52 mg/mL (176.16 mM)

form 

Solid

pka

2.65±0.10(Predicted)

color 

Light yellow to yellow

4-(3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl)-phenylamine Usage And Synthesis

Uses

CRAC intermediate 2 is a intermediate compound for CRAC inhibitor synthesis, extracted from patent WO 2013059666A1.

Synthesis

Under hydrogen atmosphere, 1-(4-nitrophenyl)-3,5-bis(trifluoromethyl)-1H-pyrazole (4.4 g, 13.5 mmol) was dissolved in EtOAc (44 mL) and Pd/C (1.3 g) was added. The reaction mixture was stirred at room temperature for 2 hours. Upon completion of the reaction, the mixture was vacuum filtered through a diatomaceous earth pad and the filter cake was washed with EtOAc. The filtrate was concentrated under reduced pressure to afford 4-(3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl)-aniline (compound 13) as a light yellow solid (3.75 g, 12.7 mmol, 94% yield). The product was characterized by 1H-NMR (300 MHz, CDCl3) and mass spectrometry (MS): 1H-NMR δ 7.22 (d, J=8.5 Hz, 2H), 7.00 (s, 1H), 6.72 (d, J=8.5 Hz, 2H); MS m/z: [M+H]+ 296.

References

[1] Journal of Organic Chemistry, 2011, vol. 76, # 16, p. 6657 - 6669
[2] Patent: WO2017/212414, 2017, A1. Location in patent: Page/Page column 43
[3] Journal of Medicinal Chemistry, 2000, vol. 43, # 16, p. 2975 - 2981

4-(3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl)-phenylamine(123066-64-8)Related Product Information

• 2,3-Dichloro-5-(trifluoromethyl)pyridine
• 2-fluoro-6-(trifluoroMethyl)benzene-1-sulfonyl chloride
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• 1-(4-NITROPHENYL)-3,5-DI(TRIFLUOROMETHYL)-1H-PYRAZOLE
• 4-(3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl)-phenylamine
• BTP2
• N1-(4-[3,5-DI(TRIFLUOROMETHYL)-1H-PYRAZOL-1-YL]PHENYL)-2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-PENTADECAFLUOROOCTANAMIDE
• 2-AZIDO-N-[4-(3,5-(BIS-TRIFLUOROMETHYL)PYRAZOL-1-YL)PHENYL] BENZAMIDE, [AZIDOANTHRANILIC ACID RING-3H]-