Acetyl iodide

Acetyl iodide is an organoiodine compound with the formula CH3COI. It is a colourless liquid. It is formally derived from acetic acid. Although far rarer in the laboratory than the related acetyl bromide and acetyl chloride, acetyl iodide is produced, transiently at least, on a far larger scale than any other acid halide. Specifically, it is generated by the carbonylation of methyl iodide in the Cativa and Monsanto processes, which are the main industrial processes that generate acetic acid. It is also an intermediate in the production of acetic anhydride from methyl acetate.

Acetyl iodide
Names
Preferred IUPAC name
Acetyl iodide
Systematic IUPAC name
Ethanoyl iodide
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.330
EC Number
  • 208-062-2
PubChem CID
UNII
UN number 1898
  • InChI=1S/C2H3IO/c1-2(3)4/h1H3 Y
    Key: LEKJTGQWLAUGQA-UHFFFAOYSA-N Y
  • InChI=1/C2H3IO/c1-2(3)4/h1H3
    Key: LEKJTGQWLAUGQA-UHFFFAOYAR
SMILES
  • CC(I)=O
Properties
C2H3IO
Molar mass 169.949 g·mol−1
Boiling point 108 °C; 226 °F; 381 K
Decomposes
Thermochemistry
Std enthalpy of
formation (ΔfH⦵298)
 -163.18--161.42 kJ mol−1
Related compounds
Related acyl halides
 Acetyl chloride
Related compounds
 Acetic acid

Acetic anhydride

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Upon treatment with carboxylic acids, acetyl iodide does not exhibit reactions typical of acyl halides, such as acetyl chloride. Instead, acetyl iodide undergoes iodide/hydroxide exchange with most carboxylic acids:

CH3COI + RCO2H → CH3CO2H + RCOI
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