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Organic compounds containing the group thiocyanate, connected through the sulfur end [R-S-CN], are referred to as thiocyanates (thiocyanic acid esters). In isothiocyantes, the attachment is through the nitrogen [R-N=C=S]. While there are several synthetic routes for alkyl thiocyanates, mostly the reaction of alkali thiocyanates with alkyl halide is followed. Thiocyanates play a vital role in the human biological system, including the biosynthesis of hypothiocyanite.
In organic chemistry, thiocyanates are widely employed in the preparation of many biologically important molecules. They can be used as reagents for the safe and selective transfer of the cyano group. For example 2-chlorobenzylthiocyanate readily transfers the cyano group to phenylacetonitrile affording melanonitrile with an excellent yield. The subsequent transfer of the cyano group to melanonitrile does not occur, in contrast to other cyanating agents. The Riemschneider thiocarbamate synthesis is one of the named reactions which involve organic thiocyanates. Aryl- and heteroarylthiocyanates find use as reagents in the activation of carboxylic acids as esters, which are then suitable for subsequent condensation reactions. Many important organic trifluoromethylthio (-SCF3) compounds can be prepared in a simple process from aliphatic, aromatic, and heterocyclic thiocyanates (Potash, S.; Rozen, S. A new synthesis of trifluoromethyl sulfides utilizing thiocyanates and fluoroform. J. Fluorine. Chem. 2014, 168, 173-176).