Synlett 2013; 24(9): 1160-1161
DOI: 10.1055/s-0033-1338941
© Georg Thieme Verlag Stuttgart · New York


Rajni Sharma
Natural Product Chemistry, Indian Institute of Integrative Medicine (CSIR), Canal Road, Jammu 18001, India   Email:
› Author Affiliations
Further Information

Publication History

Publication Date:
08 May 2013 (online)


Chloroacetonirile is a simple organic compound with a linear chemical structure. Both ends of this molecule have a reactive group: a cyano group on one side and a chloro substituent on the other side. The nitrile can be converted into an amine, amide, amidine, etc., whereas the chloro group plays an important role in different alkylation reactions. Choloacetonitrile is known for the synthesis of ­heterocycles including thiophenes,[1] thiazoles[2] and thiazolo[3,2-b][1,2,4]triazoles.[3] Chloroacetonitrile is commercially available and can be synthesized by dehydration of chloroacetamide with phosphorous pentoxide.[4]

Zoom Image
Scheme 1
  • References

  • 1 Fadda AA, Latif AE, El-Mekawy R. Eur. J. Med. Chem. 2009; 44: 1250
  • 2 Thomae D, Perspicace E, Xu Z, Henryon D, Schneider S, Hesse S, Kirsch G, Seck P. Tetrahedron 2009; 65: 2982
  • 3 El-Sherief HA. H, Hozien ZA, El-Mahdy AF. M, Sarhan AA. O. ARKIVOC 2011; (x): 71
  • 4 Reisner DB, Homing EC. Org. Synth. 1963; Coll. Vol. 4: 144
  • 5 Castellanos L, Duque C, Rodriguez J, Jimenez C. Tetrahedron 2007; 63: 1544
  • 6 Legeay JC, Eynde JJ. V, Bazureau JP. Tetrahedron Lett. 2007; 48: 1063
  • 7 Lebeuf R, Robert F, Landais Y. Org. Lett. 2005; 7: 4557
  • 8 Yadav MR, Grande F, Chouhan BS, Naik PP, Giridhar R, Garofalo A, Neamati N. Eur. J. Med. Chem. 2012; 48: 231
  • 9 Bayoumi A, Ghiaty A, El-Morsy A, Abdul-Khair H, Hassan MH, Elmeligie S. Bull. Fac. Pharm. 2012; 50: 141
  • 10 Hirose M, Okaniwa M, Miyazaki T, Imada T, Ohasi T, Tanaka Y, Arita T, Yabuki M, Kawamoto T, Tsutumi S, Sumita A, Takagi T, Bi-Ching S, Yano J, Aertgeerts K, Yoshida S, Ishikawa T. Bioorg. Med. Chem. 2012; 20: 5600
  • 11 Zhang S.-L, Damu GL.V, Geng R.-X, Zhou CH. Eur. J. Med. Chem. 2012; 55: 164
  • 12 Torres E, Duque MD, Lopez-Querol M, Taylor MC, Naesens L, Ma C, Pinto LH, Sureda FX, Vázquez S. Bioorg. Med. Chem. 2012; 20: 942
  • 13 Fugel W, Oberholzer AE, Gschloessl B, Dzikowski B, Pressburger N, Preu L, Pearl LH, Baratte B, Ratin M, Okun I, Doerig C, Kruggel S, Lemcke T, Meijer L, Kunick C. J. Med. Chem. 2013; 56: 264