4-Chlorobutyronitrile
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| Names | |
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| Other names
4-chlorobutanenitrile
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.010.029 |
| EC Number |
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PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| 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: | |
 
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| 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
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3-Chloropropionitrile Butyronitrile |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.
Synthesis
[edit]
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
[edit]4-Chlorobutyronitrile is a precursor to the drugs buflomedil and buspirone.[4]
Precursor
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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]
References
[edit]- ^ Charles F. H. Allen (1928). "γ-Chlorobutyronitrile". Organic Syntheses. 8: 52. doi:10.15227/orgsyn.008.0052.
- ^ Schlatter, M. J. (1943). "Cyclopropyl Cyanide". Organic Syntheses. 23: 20. doi:10.15227/orgsyn.023.0020.
- ^ J Bacha & C Selwitz, U.S. patent 3,843,709 (1974 to Chevron USA Inc).
- ^ 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. ISBN 3527306730.
- ^ Craig, Lyman 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.
- ^ Zhang, Ying; Kong, Duanyang; Wang, Rui; Hou, Guohua (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. PMID 28294268.
- ^ "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.