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Oxalyl chloride is a chemical compound with the formula (COCl)2. It is a colorless liquid with a pungent, irritating odor. Oxalyl chloride is highly reactive and is used as a reagent in organic synthesis. It is particularly useful for converting carboxylic acids into acyl chlorides, which are important intermediates in the synthesis of esters, amides, and other functional groups.

The preparation of oxalyl chloride typically involves the reaction of oxalic acid with phosphorus pentachloride or thionyl chloride. It is also produced by the chlorination of oxalyl bromide. Due to its reactivity, oxalyl chloride must be handled with care, as it reacts violently with water and can decompose to produce toxic gases. It is corrosive and can cause severe burns to skin and eyes. Inhalation of its vapors can lead to respiratory irritation and damage.

In organic chemistry, oxalyl chloride is often used in conjunction with dimethyl sulfoxide (DMSO) in the Swern oxidation, a method for oxidizing primary and secondary alcohols to aldehydes and ketones, respectively. The reaction proceeds under mild conditions and is often preferred over other oxidation methods that may be harsher or less selective. Oxalyl chloride is also employed in the preparation of various heterocycles and in the synthesis of complex organic molecules. Its utility stems from its ability to readily form acyl chlorides, which are highly electrophilic and participate in a wide range of reactions.