Acetyl iodide

Acetyl iodide

Skeletal formula of acetyl iodide Spacefill model of acetyl iodide
Names
Preferred IUPAC name Ethanoyl iodide
Systematic IUPAC name Acetyl iodide
Identifiers
CAS Number	507-02-8 N
ChemSpider	10051 Y
EC Number	208-062-2
Jmol 3D model	Interactive image
PubChem	10483
UN number	1898
InChI 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
Chemical formula	C2H3IO
Molar mass	169.95 g·mol−1
Boiling point	108 °C; 226 °F; 381 K
Solubility in water	Decomposes
Thermochemistry
Std enthalpy of formation (ΔfHo298)	-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

Acetyl iodide is an organoiodine compound with the formula CH₃C(O)I. 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 that are the main industrial route to acetic acid. 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, such as acetyl chloride. Instead, acetyl iodide undergoes iodide/hydroxide exchange with most carboxylic acids:

CH₃C(O)I + RCO₂H → CH₃CO₂H + RC(O)I