3-Cyclopropyl-3-oxopropanenitrile Chemical Properties

Boiling point:

124-128 °C(Press: 21 Torr)

Density 

1.156±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Store in freezer, under -20°C

pka

9.90±0.20(Predicted)

Appearance

Colorless to light yellow Liquid

InChI

InChI=1S/C6H7NO/c7-4-3-6(8)5-1-2-5/h5H,1-3H2

InChIKey

SDARMQNRQJBGQE-UHFFFAOYSA-N

SMILES

C1(C(CC#N)=O)CC1

Safety Information

HS Code 

2926907090

3-Cyclopropyl-3-oxopropanenitrile Usage And Synthesis

Uses

β-oxo-Cyclopropylpropanenitrile is used in the synthesis of novel 5-amino pyrazole derivatives against carcinogenesis present in breast cancer cell lines. Also aids in the structure based design and synthesis of N-pyrazole and N’-thiazole urea inhibitors of MAP kinase p38α.

Uses

3-cyclopropyl-3-oxopropanenitrile is used in the synthesis of novel 5-amino pyrazole derivatives against carcinogenesis present in breast cancer cell lines. Also aids in the structure based design and s ynthesis of N-pyrazole and N’thiazole urea inhibitors of MAP kinase p38α.

Synthesis

Example 1 Synthesis of 3-cyclopropyl-3-oxopropanenitrile: To a mechanically stirred solution of 15.0 g (176 mmol) of cyanoacetic acid and 100 mg of 1,10-phenanthroline dissolved in 500 mL of THF was slowly added 141 mL (352 mmol) of 2.5 M n-butyllithium in hexane solution at -78 °C. The reaction system was slowly warmed to 0°C in a water bath and held for 15 minutes until most of the brown color faded. Subsequently, the mixture was re-cooled to -78 °C and 8.0 mL (88 mmol) of cyclopropylcarbonyl chloride dissolved in 8 mL of THF was added dropwise. The reaction mixture was gradually warmed to room temperature and stirring was continued for 15 minutes. The reaction solution was poured into 300mL of 5% HCl aqueous solution and extracted three times with ether. The organic phases were combined, washed sequentially with saturated aqueous sodium bicarbonate and brine, and dried over anhydrous magnesium sulfate. After concentration under reduced pressure, it was purified by silica gel column chromatography using a hexane solution of 30% ethyl acetate as eluent to give 6.5 g (54% yield) of the target product 3-cyclopropyl-3-oxopropanenitrile. The product was stored with 1% w/w BHT in 40 mL of dichloromethane at -5 °C. TLC detection (20% ethyl acetate/hexane, Rf 0.12) showed green coloration with ninhydrin staining; 1H-NMR (300 MHz, CDCl3): δ 3.63 (s, 2H), 2.10 (m, 1H), 1.20 (m, 2H), 1.10 (m, 2H).

References

[1] Patent: US5250521, 1993, A
[2] Patent: US5260285, 1993, A

3-Cyclopropyl-3-oxopropanenitrile(118431-88-2)Related Product Information

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