4-Chlorobutyronitrile

4-Chlorobutyronitrile is the organic compound with the formula ClCH₂CH₂CH₂CN. With both chloro and cyano functional groups, it is a bifunctional molecule. It is a colorless liquid.

4-Chlorobutyronitrile

Names
Other names 4-chlorobutanenitrile
Identifiers
CAS Number	628-20-6 Y
3D model (JSmol)	Interactive image
ChemSpider	11831
ECHA InfoCard	100.010.029
EC Number	211-031-6
PubChem CID	12336
UNII	9JDK6275GP
CompTox Dashboard (EPA)	DTXSID0060850
InChI InChI=1S/C4H6ClN/c5-3-1-2-4-6/h1-3H2 Key: ZFCFBWSVQWGOJJ-UHFFFAOYSA-N
SMILES C(CC#N)CCl
Properties
Chemical formula	C4H6ClN
Molar mass	103.55 g·mol−1
Appearance	colorless liquid
Density	1.0934 g/cm3 @15 °C
Boiling point	189–191 °C (372–376 °F; 462–464 K)
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H315, H319, H335
Precautionary statements	P261, P264, P270, P271, P280, P301+P310, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501
Related compounds
Related compounds	3-Chloropropionitrile Butyronitrile
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Synthesis

Synthesis:^[1]

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.^[2] However an increased yield was reported when the base/solvent mixture was changed to NaOH/DMSO.^[3]

Drug use

4-Chlorobutyronitrile is a precursor to the drugs buflomedil and buspirone.^[4]

Precursor

Synthesis:^[5] Stereoselective:^[6]

4-Chlorobutyronitrile has been used as a starting material to prepare 2-phenylpyrrolidine [registry number 1006-64-0]. 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 all of the known codenamed examples includes the following: JNJ-7925476, McN5652, Mcn-5292, Mcn 5707, McN-5908, McN 4612-z, McN-5558 & McN-5847.

More recently, an alternative synthetic protocol was also reported by Maryanoff.^[7]