Synlett 2009(12): 2035-2036  
DOI: 10.1055/s-0029-1217441
SPOTLIGHT
© Georg Thieme Verlag Stuttgart ˙ New York

Potassium Thiocyanate (KSCN): A Versatile Reagent

Soheil Sayyahi
Chemistry Department, College of Science, Chamran University, Ahvaz 61357-4-3169, Iran
e-Mail: sayyahi.soheil@gmail.com;
Further Information

Publication History

Publication Date:
03 July 2009 (online)

Introduction

Potassium thiocyanate (KSCN) is a white odorless, crystalline powder, slightly hydroscopic, and commercially available reagent. It is readily soluble in water and stable under normal temperature and pressure (mp: 173 ˚C, d = 1.89 g/cm³). Since sulfur-containing groups serve as an important auxiliary function in synthetic sequences, [¹] potassium thiocyanate is widely used as a transfer reagent for sulfur in various organic transformations. [²] The hypervalent iodine(III) in combination with potassium thio­cyanate and diphenyl diselenide promoted a multicomponent reaction for the synthesis of phenylselenyl thiocyanates and isothiocyanates from alkenes. [³] Various tosyl and ­bromo derivatives of Cbz-, Boc-, and Fmoc-protected threonine methyl esters have been subjected to nucleophilic substitution with potassium thiocyanate in acetonitrile for the synthesis of allo- and threo-3,3′-dimethylcystine derivatives. [4] This reagent is supported on silica gel and applied for thiocyanation of β-dicarbonyl compounds and the synthesis of 2-aminothiazoles. [5] Recently, potassium thiocyanate is used for the conversion of alkyl halides into alkyl thiocyanate in water under phase-transfer catalysis. [6] It is also employed for the ­synthesis of 1-aroyl-3-(substituted-2-benzothiazolyl)thioureas with antibacterial properties. [7]

    References

  • 1 Kondo T. Mitsudo TA. Chem. Rev.  2000,  100:  3205 
  • 2 Erian AW. Sherif SM. Tetrahedron  1999,  55:  7957 
  • 3 Margarita R. Mercanti C. Parlanti L. Piancatelli G. Eur. J. Org. Chem.  2000,  1865 
  • 4 Nasir Baig RB. Sai Sudhir V. Chandrasekaran S. Tetrahedron: Asymmetry  2008,  19:  1425 
  • 5 Kodomari M. Aoyama T. Suzuki Y. Tetrahedron Lett.  2002,  43:  1717 
  • 6 Kiasat AR. Badri R. Sayyahi S. Chin. Chem. Lett.  2008,  19:  1301 
  • 7 Saeed A. Rafique H. Hameed A. Rasheed S. Pharm. Chem. J.  2008,  42:  191 
  • 8 Das B. Saidi Reddy V. Krishnaiah M. Tetrahedron Lett.  2006,  47:  8471 
  • 9 Reddy S. Nagavani S. Heteroatom Chem.  2008,  19:  97 
  • 10a Aoyama T. Murata S. Nagata Y. Takidoa T. Kodomari M. Tetrahedron Lett.  2005,  46:  4875 
  • 10b Aoyama T. Murata S. Arai I. Araki N. Takidoa T. Suzuki Y. Kodomari M. Tetrahedron  2006,  62:  3201. 
  • 11 Reddy SM. Narender M. Nageswar YVD. Rao KR. Tetrahedron Lett.  2005,  46:  6437 
  • 12 Tao XL. Lei M. Wang YG. Synthetic Commun.  2007,  37:  399 
  • 13 Minakata S. Hotta T. Oderaotoshi Y. Komatsu M. J. Org. Chem.  2006,  71:  7471 
  • 14 Ju Y. Kumar D. Varma RS. J. Org. Chem.  2006,  71:  6697