Acetyl iodide is an

organoiodine compound Organoiodine compounds are organic compounds that contain one or more carbon–iodine bonds. They occur widely in organic chemistry, but are relatively rare in nature. The thyroxine hormones are organoiodine compounds that are required for he ...

with the formula CH₃COI. It is a colourless liquid. It is formally derived from

acetic acid Acetic acid , systematically named ethanoic acid , is an acidic, colourless liquid and organic compound with the chemical formula (also written as , , or ). Vinegar is at least 4% acetic acid by volume, making acetic acid the main componen ...

. Although far rarer in the laboratory than the related acetyl bromide and

acetyl chloride Acetyl chloride (CH3COCl) is an acyl chloride derived from acetic acid. It belongs to the class of organic compounds called acid halides. It is a colorless, corrosive, volatile liquid. Its formula is commonly abbreviated to AcCl. Synthesis On ...

, acetyl iodide is produced, transiently at least, on a far larger scale than any other acid halide. Specifically, it is generated by the

carbonylation Carbonylation refers to reactions that introduce carbon monoxide into organic and inorganic substrates. Carbon monoxide is abundantly available and conveniently reactive, so it is widely used as a reactant in industrial chemistry. The term carbo ...

methyl iodide Iodomethane, also called methyl iodide, and commonly abbreviated "MeI", is the chemical compound with the formula CH3I. It is a dense, colorless, volatile liquid. In terms of chemical structure, it is related to methane by replacement of one ...

in the Cativa and Monsanto processes, which are the main industrial processes that generate

. It is also an intermediate in the production of acetic anhydride from methyl acetate. Upon treatment with carboxylic acids, acetyl iodide does not exhibit reactions typical of

acyl halides In organic chemistry, an acyl halide (also known as an acid halide) is a chemical compound derived from an oxoacid by replacing a hydroxyl group () with a halide group (, where X is a halogen). If the acid is a carboxylic acid (), the compoun ...

, such as acetyl chloride. Instead, acetyl iodide undergoes iodide/hydroxide exchange with most

carboxylic acid In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an R-group. The general formula of a carboxylic acid is or , with R referring to the alkyl, alkenyl, aryl, or other group. Carboxyl ...

s: :

References

{{Reflist Acyl iodides