2-Chloroethyl thiocyanate

Chloroethyl thiocyanate, ClCHjCHiSCN (1). Mol. wt. 121.58, b.p. 87 88 /18 mm. This substance is obtained by reaction of potassium thiocyanate with l-bromo-2-chloroethane in refluxing methanol (77-88% yield). 

In solution in chloroform or toluene, the reagent adds rapidly to ethylene or to cyclohexene at —60° to give 2-chloroethyl thiocyanate or 2-chlorocyclohexyl thiocyanate, both in yield of about 80%. ... 

Ethylene sulfide was first prepared by Dele pine [47] by the action of aqueous sodium sulfide with 2-chloroethyl thiocyanate. The best laboratory method involves the reaction of epoxides with either thiourea or potassium thiocyanate [48], These and more recent methods are described in Scheme 3. 

Another example of soft nucleophile attack according to the H5AB theory was given by the reaction of thiocyanate salts with 1-chloroethyl carbonates affording the corresponding 1-thiocyano and/or 1-isothiocyano ethyl carbonates in good yields (Ref. 101). 

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