Acetyl iodide

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Acetyl iodide
Skeletal formula of acetyl iodide
Skeletal formula of acetyl iodide
Spacefill model of acetyl iodide
Spacefill model of acetyl iodide
Names
Preferred IUPAC name
Acetyl iodide[1]
Systematic IUPAC name
Ethanoyl iodide
Identifiers
3D model (
JSmol
)
ChemSpider
ECHA InfoCard
 100.007.330 Edit this at Wikidata
EC Number
  • 208-062-2
UNII
UN number 1898
  • InChI=1S/C2H3IO/c1-2(3)4/h1H3 checkY
    Key: LEKJTGQWLAUGQA-UHFFFAOYSA-N checkY
  • InChI=1/C2H3IO/c1-2(3)4/h1H3
    Key: LEKJTGQWLAUGQA-UHFFFAOYAR
  • 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 checkY☒N ?)

Acetyl iodide is an

methyl iodide in the Cativa and Monsanto processes, which are the main industrial processes that generate acetic acid.[2] It is also an intermediate in the production of acetic anhydride from methyl acetate.[3]

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:[4]

CH3COI + RCO2H → CH3CO2H + RCOI

References

  1. ^ "ACETYL IODIDE - PubChem Public Chemical Database". The PubChem Project. USA: National Center for Biotechnology Information.
  2. Platinum Metals Rev. 44 (3): 94–105. Archived from the original
    (PDF) on 2015-09-24. Retrieved 2011-07-03.
  3. doi:10.1016/0920-5861(92)80188-S
  4. S2CID 97920158
    .
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