Most of the reactivity of thioacetic acid arises from the conjugate base, thioacetate. Salts of this anion, e.g. potassium thioacetate, are used to generate thioacetate esters. Thioacetate esters undergo hydrolysis to give thiols. A typical method for preparing a thiol from an alkyl halide using thioacetic acid proceeds in four discrete steps, some of which can be conducted sequentially in the same flask:
:, where X = Cl, Br, I
In an application that illustrates the use of its radical behavior, thioacetic acid is used with AIBN in a free radical mediated nucleophilic addition to an exocyclic alkene forming a thioester: