ChemicalBook CAS DataBase List Cyclopropanecarbonitrile

Cyclopropanecarbonitrile synthesis

8synthesis methods

Product Name:Cyclopropanecarbonitrile
CAS Number:5500-21-0
Molecular formula:C4H5N
Molecular Weight:67.09

There are many methods for synthesizing cyclopropaneformitrile. A common industrial synthetic route uses 4-chlorobutyronitrile as a starting material and carries out an intramolecular cyclization reaction under alkaline conditions (such as sodium hydroxide (NaOH)) to generate a cyclopropane ring.

628-20-6 Synthesis

628-20-6
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$10.00/10g

5500-21-0
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$16.00/5mL

Yield:5500-21-0 98%

Reaction Conditions:

with hydrogenchloride;sodium hydroxide;sodium chloride in water;dimethyl sulfoxide

Steps:

1 Preparation of cyclopropylnitrile (2 molar scale) STR2
EXAMPLE 1 Preparation of cyclopropylnitrile (2 molar scale) STR2 A stirred mixture of 4-chlorobutyronitrile (213.4 g, 2.0 mole), sodium chloride (58.0 g, 0.5 mole) and 2.0 g of water in 200 g of dimethylsulfoxide is heated to 80° C., treated with ground solid sodium hydroxide (88 g, 2.2 mole) over a 3 hour period and held at 80° C. for about 1 additional hour. The reaction mixture is cooled to room temperature neutralized to about pH6.8 with concentrated HCl (37% aqueous solution), diluted with 200 ml water (readjusted pH to 6.8 with 37% HCl) and azeotropically distilled with a Dean Stark trap to remove the cyclopropylnitrile/water azeotrope. The aqueous layer is continuously returned to the distillation pot to give the initial product as the distillate cyclopropylnitrile, 133.5 g. A 121.5 g sample of this cyclopropylnitrile is azeotropically distilled using a Dean Stark trap (to remove water) and continuous return of the organic layer to give the final productproduct cyclopropylnitrile, 106.6. g, 87.8% yield, 98% pure by GLC analysis and 0.04% H₂ O by Karl Fischer titration.

References:

American Cyanamid Company US5380911, 1995, A

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5332-06-9 Synthesis