3,3-DIFLUORO-CYCLOBUTANECARBONITRILE Chemical Properties

Boiling point:

160.5±40.0 °C(Predicted)

Density 

1.19±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

Appearance

Colorless to light yellow Solid

InChI

InChI=1S/C5H5F2N/c6-5(7)1-4(2-5)3-8/h4H,1-2H2

InChIKey

RCXLAPBURAMYKG-UHFFFAOYSA-N

SMILES

C1(C#N)CC(F)(F)C1

Safety Information

HS Code 

2926907090

3,3-DIFLUORO-CYCLOBUTANECARBONITRILE Usage And Synthesis

Synthesis

The general procedure for the synthesis of 3,3-difluorocyclobutanecarbonitrile from 3-oxocyclobutanecarbonitrile was as follows: Example 125A (8.21 g, 86 mmol) was dissolved in dichloromethane (135 mL), stirred and cooled to <10 °C at room temperature. DAST (11.41 mL, 86 mmol) was slowly added, followed by warming the reaction mixture to room temperature. Stirring was continued at room temperature for 2 hours. Upon completion of the reaction, the mixture was poured into saturated aqueous NaHCO3 solution (200 mL) for quenching and partitioning. The aqueous phase was extracted with dichloromethane (2 x 50 mL). The organic phases were combined, dried over anhydrous Na2SO4, filtered and concentrated to give Example 125B (9.14 g, 78 mmol, 90% yield) as a brown oil. The product was characterized by XH NMR (400 MHz, CDC13) with chemical shifts of 3.06-2.91 (m, 5H).

References

[1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 13, p. 3947 - 3953
[2] Patent: WO2015/115673, 2015, A1. Location in patent: Page/Page column 88-89
[3] Patent: WO2013/62964, 2013, A2. Location in patent: Paragraph 1267; 1268
[4] Patent: US2014/80803, 2014, A1. Location in patent: Paragraph 1134
[5] Patent: US2017/50961, 2017, A1. Location in patent: Paragraph 1065; 1066; 1067; 1068

3,3-DIFLUORO-CYCLOBUTANECARBONITRILE(86770-80-1)Related Product Information

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