4-Chlorobutyronitrile is the organic compound with the formula ClCH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>CN. With both chloro and cyano functional groups, it is a bifunctional molecule. It is a colorless liquid.
It is prepared by the reaction of potassium cyanide with 1-bromo-3-chloropropane.
Cyclopropyl cyanide is prepared by reaction of 4-chlorobutyronitrile with sodium amide in liquid ammonia. However an increased yield was reported when the base/solvent mixture was changed to NaOH/DMSO.
4-Chlorobutyronitrile is a precursor to the drugs buflomedil and buspirone.
4-Chlorobutyronitrile has been used as a starting material to prepare 2-phenylpyrrolidine. This in turn is a chief precursor to a family of compounds called pyrroloisoquinolines. These are valuable agents in medicinal chemistry that are endowed with BAT substrate reuptake inhibitor properties, elevating the synaptic concentration of serotonin and/or catecholamines. They therefore have application in the treatment of CNS diseases and eating disorders. A list of the known development codes includes the following: JNJ-7925476, McN5652, Mcn-5292, McN 5707, McN-5908, McN-4612, McN-5558, and McN-5847.
More recently, an alternative synthetic protocol was also reported by Maryanoff.