2,4-DIFLUORO-5-NITROBENZONITRILE Chemical Properties

Boiling point:

271.5±40.0 °C(Predicted)

Density 

1.51±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

Appearance

Off-white to light yellow Solid

Safety Information

Hazard Codes 

Xi

Hazard Note 

Irritant

HS Code 

2926907090

2,4-DIFLUORO-5-NITROBENZONITRILE Usage And Synthesis

Chemical Properties

white powder

Uses

2,4-Difluoro-5-nitrobenzonitrile is used in the synthesis of potent and selective tankyrase inhbitors used in the inhibition of tumorigenesis.

Synthesis

General procedure for the synthesis of 2,4-difluoro-5-nitrobenzonitrile from 2,4-difluorobenzonitrile: Potassium nitrate (16.4 g, 147.4 mmol) was slowly added to concentrated sulfuric acid (85 ml, 1582 mmol) at 0 °C, followed by 2,4-difluorobenzonitrile (11.0 g, 79.1 mmol) dropwise. The reaction mixture was stirred at this temperature for 4 hours. Upon completion of the reaction, the mixture was quenched by pouring into ice/water (800 mL). The precipitated solid product was collected by filtration and dried to give 2,4-difluoro-5-nitrobenzonitrile (13.8 g, 95% yield) as a white solid. The product was confirmed by NMR hydrogen spectrum (400 MHz, CDCl3): δ 8.48 (m, 1H), 7.24 (m, 1H).

References

[1] Patent: WO2006/87530, 2006, A1. Location in patent: Page/Page column 59
[2] Patent: WO2005/103010, 2005, A2. Location in patent: Page/Page column 40
[3] Patent: CN106854165, 2017, A. Location in patent: Paragraph 0106; 0107; 0138; 0139
[4] Journal of Medicinal Chemistry, 1994, vol. 37, # 4, p. 467 - 475
[5] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 15, p. 2019 - 2022

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