CH2ICOOH

CH2ICOOH is the chemical formula for iodoacetic acid. It is a simple organic compound that is a derivative of acetic acid, where one of the hydrogen atoms on the methyl group has been replaced by an iodine atom. Iodoacetic acid is a colorless crystalline solid with a pungent odor. It is soluble in water and ethanol.

The primary reactivity of iodoacetic acid stems from the carbon-iodine bond. Iodine is a good leaving group, making the methylene carbon electrophilic and susceptible to nucleophilic attack. This property is exploited in various biochemical and chemical applications. In biochemistry, iodoacetic acid is frequently used as an alkylating agent to inhibit enzymes that contain cysteine residues in their active sites. It reacts with the thiol group of cysteine to form a stable thioether linkage, thereby irreversibly inactivating the enzyme. This makes it a valuable tool for studying enzyme mechanisms and protein structure.

In organic synthesis, iodoacetic acid and its esters can be used in alkylation reactions, though less commonly than other haloacetic acid derivatives due to the higher cost and potential instability of the iodine-containing compound. It can also be a precursor for the synthesis of other iodo-organic compounds. Due to its reactivity and toxicity, iodoacetic acid should be handled with appropriate safety precautions.