CH3CH2SO2Cl

CH3CH2SO2Cl, commonly known as ethanesulfonyl chloride, is an organosulfur compound belonging to the sulfonyl chloride class. It features a sulfonyl group (SO2) bonded to a chlorine atom and an ethyl group (CH3CH2–). This colorless to pale yellow liquid is highly reactive and commonly used as an intermediate in organic synthesis.

Ethanesulfonyl chloride is synthesized primarily through the chlorination of ethanesulfonic acid or its derivatives, often using thionyl chloride (SOCl2) as a reagent. Its structure consists of a central sulfur atom double-bonded to two oxygen atoms and single-bonded to a chlorine atom and an ethyl moiety. The compound exhibits polar characteristics due to the electronegative sulfur and oxygen atoms, influencing its solubility and reactivity.

In organic synthesis, ethanesulfonyl chloride serves as a sulfonylating agent, facilitating the introduction of sulfonyl groups into various substrates. It is particularly useful in the preparation of sulfonamides, sulfones, and other sulfonyl-containing compounds. The compound’s reactivity stems from the labile sulfonyl chloride functional group, which can undergo nucleophilic substitution reactions readily.

Applications of ethanesulfonyl chloride extend to pharmaceutical and agrochemical industries, where sulfonyl derivatives play critical roles in drug design and pest control. However, its use requires careful handling due to its corrosive nature and potential toxicity. Proper ventilation and protective equipment are essential when working with this compound to minimize exposure risks.

Stability-wise, ethanesulfonyl chloride should be stored under inert atmospheric conditions, such as nitrogen or argon, to prevent hydrolysis or decomposition. It is typically kept refrigerated to extend shelf life, as prolonged exposure to moisture or heat can degrade the compound. Its properties, including a boiling point of approximately 190–195°C and a density of around 1.35 g/cm³, further characterize its behavior in laboratory settings.