2-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)acetonitrile Chemical Properties

Boiling point:

249.4±40.0 °C(Predicted)

Density 

1.43±0.1 g/cm3(Predicted)

storage temp. 

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

solubility 

DMSO (Sparingly), Ethyl Acetate (Slightly), Methanol (Slightly)

form 

Oil

color 

Pale Yellow

2-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)acetonitrile Usage And Synthesis

Synthesis

General procedure for the synthesis of (2,2-difluoro-benzo[1,3]dioxol-5-yl)-acetonitrile from 5-(chloromethyl)-2,2-difluorobenzo[d][1,3]dioxol-5-yl: To a solution of 5-(chloromethyl)-2,2-difluoro-1,3-benzo[d][1,3]dioxol-5-yl (1 eq.) in DMSO (1 vol.), NaCN (1.4 eq.) in a suspension in DMSO (3 vol), keeping the reaction temperature between 30-40 °C. The reaction mixture was stirred for 1 h and then water (6 vol) and methyl tert-butyl ether (MTBE, 4 vol) were added. The organic and aqueous layers were separated and the aqueous layer was further extracted with MTBE (1.8 vol). All organic layers were combined, washed with water (1.8 v/v) and subsequently dried over anhydrous sodium sulfate, filtered and concentrated to afford the crude product (2,2-difluoro-1,3-benzodioxol-5-yl)-acetonitrile in 95% yield. The crude product did not require further purification and could be used directly in the subsequent reaction step. The subsequent steps were the same as those described above for the acid portion of the synthesis.

References

[1] Patent: US2012/15999, 2012, A1
[2] Patent: WO2016/109362, 2016, A1. Location in patent: Paragraph 00160
[3] Patent: US2011/98311, 2011, A1
[4] Patent: US2011/98311, 2011, A1
[5] Patent: US2011/98311, 2011, A1

2-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)acetonitrile(68119-31-3)Related Product Information

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