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
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.010.029
EC Number
  • 211-031-6
UNII
  • InChI=1S/C4H6ClN/c5-3-1-2-4-6/h1-3H2
    Key: ZFCFBWSVQWGOJJ-UHFFFAOYSA-N
  • C(CC#N)CCl
Properties
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:
GHS06: ToxicGHS07: Exclamation mark
Danger
H301, H315, H319, H335
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 [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 subtrate 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]

References
  1. Charles F. H. Allen (1928). "γ-Chlorobutyronitrile". Organic Syntheses. 8: 52. doi:10.15227/orgsyn.008.0052.
  2. Schlatter, M. J. (1943). "Cyclopropyl Cyanide". Organic Syntheses. 23: 20. doi:10.15227/orgsyn.023.0020.
  3. J Bacha & C Selwitz, U.S. Patent 3,843,709 (1974 to Chevron USA Inc).
  4. Pollak, Peter; Romeder, Gérard; Hagedorn, Ferdinand; Gelbke, Heinz-Peter (2000). "Nitriles". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_363.
  5. Craig, L. C., Bulbrook, Helen., Hixon, R. M. (May 1931). "A GENERAL METHOD OF SYNTHESIS FOR ALPHA-SUBSTITUTED PYRROLINES AND PYRROLIDINES". Journal of the American Chemical Society. 53 (5): 1831–1835. doi:10.1021/ja01356a028.
  6. Zhang, Y., Kong, D., Wang, R., Hou, G. (2017). "Synthesis of chiral cyclic amines via Ir-catalyzed enantioselective hydrogenation of cyclic imines". Organic & Biomolecular Chemistry. 15 (14): 3006–3012. doi:10.1039/C7OB00442G.
  7. "N-VINYLPYRROLIDIN-2-ONE AS A 3-AMINOPROPYL CARBANION EQUIVALENT IN THE SYNTHESIS OF SUBSTITUTED 1-PYRROLINES: 2-PHENYL-1-PYRROLINE". Organic Syntheses. 75: 215. 1998. doi:10.15227/orgsyn.075.0215.
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