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[1]
Identifiers
CAS Number	507-02-8 ;
3D model (JSmol)	Interactive image;
ChemSpider	10051 ;
ECHA InfoCard	100.007.330
EC Number	208-062-2;
PubChem CID	10483;
UNII	JAL3KV9I1O ;
UN number	1898
CompTox Dashboard (EPA)	DTXSID0060141 ;
	InChI InChI=1S/C2H3IO/c1-2(3)4/h1H3 Key: LEKJTGQWLAUGQA-UHFFFAOYSA-N ; InChI=1/C2H3IO/c1-2(3)4/h1H3 Key: LEKJTGQWLAUGQA-UHFFFAOYAR;
	SMILES CC(I)=O;
Properties
Chemical formula	C2H3IO
Molar mass	169.949 g·mol−1
Boiling point	108 °C; 226 °F; 381 K
Solubility in water	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).
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	Infobox references

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 that are the main industrial route to 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

"ACETYL IODIDE - PubChem Public Chemical Database". The PubChem Project. USA: National Center for Biotechnology Information.
Jones, J. H. (2000). "The Cativa^TM Process for the Manufacture of Acetic Acid" (PDF). Platinum Metals Rev. 44 (3): 94–105.
Zoeller, J. R.; Agreda, V. H.; Cook, S. L.; Lafferty, N. L.; Polichnowski, S. W.; Pond, D. M. (1992), "Eastman Chemical Company Acetic Anhydride Process", Catal. Today, 13 (1): 73–91, doi:10.1016/0920-5861(92)80188-S
M. G. Voronkov; L. I. Belousova; A. A. Trukhina; N. N. Vlasova (2003). "Acyl Iodides in Organic Synthesis: IV. Reaction of Acetyl Iodide with Carboxylic Acids". Russian Journal of Organic Chemistry. 39 (12): 1702. doi:10.1023/B:RUJO.0000019730.43667.46.

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[1] "ACETYL IODIDE - PubChem Public Chemical Database". The PubChem Project. USA: National Center for Biotechnology Information.

[Cativa-2] Jones, J. H. (2000). "The Cativa^TM Process for the Manufacture of Acetic Acid" (PDF). Platinum Metals Rev. 44 (3): 94–105.

[3] Zoeller, J. R.; Agreda, V. H.; Cook, S. L.; Lafferty, N. L.; Polichnowski, S. W.; Pond, D. M. (1992), "Eastman Chemical Company Acetic Anhydride Process", Catal. Today, 13 (1): 73–91, doi:10.1016/0920-5861(92)80188-S

[4] M. G. Voronkov; L. I. Belousova; A. A. Trukhina; N. N. Vlasova (2003). "Acyl Iodides in Organic Synthesis: IV. Reaction of Acetyl Iodide with Carboxylic Acids". Russian Journal of Organic Chemistry. 39 (12): 1702. doi:10.1023/B:RUJO.0000019730.43667.46.