tetraethylammonium iodide
{{Chembox
| ImageFile = Tetraethylammonium iodide.svg
| ImageSize = 200px
| PIN = N,N,N-Triethylethanaminium iodide
| OtherNames = Tetamon iodide; Tetramon J; TEAI
|Section1={{Chembox Identifiers
| CASNo = 68-05-3
| PubChem = 6225
| ChemSpiderID = 5990
| SMILES = [I-].CC[N+](CC)(CC)CC
| InChI = 1/C8H20N.ClH/c1-5-9(6-2,7-3)8-4;/h5-8H2,1-4H3;1H/q+1;/p-1
| InChIKey = UQFSVBXCNGCBBW-UHFFFAOYSA-M
| StdInChI = InChI=1S/C8H20N.HI/c1-5-9(6-2,7-3)8-4;/h5-8H2,1-4H3;1H/q+1;/p-1
| StdInChIKey = UQFSVBXCNGCBBW-UHFFFAOYSA-M
}}
|Section2={{Chembox Properties
| C=8 | H=20 | I=1 | N=1
| Appearance = Colorless or yellowish crystalline solid
| Density = 1.566 g/cm3The Merck Index, 10th Ed., p.1316, Rahway: Merck & Co.
| MeltingPtC = 280
| MeltingPt_notes = (decomposes)
| BoilingPt =
| Solubility = soluble
}}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}
}}
Tetraethylammonium iodide is a quaternary ammonium compound with the chemical formula C8H20N+I−. It has been used as the source of tetraethylammonium ions in pharmacological and physiological studies, but is also used in organic chemical synthesis.
Chemistry
=Preparation=
Tetraethylammonium iodide is commercially available, but can be prepared by the reaction between triethylamine and ethyl iodide.A. A. Vernon and J. L. Sheard (1948). "The solubility of tetraethylammonium iodide in benzene-ethylene dichloride mixtures." J. Am. Chem. Soc. 70 2035-2036. https://doi.org/10.1021/ja01186a015
=Structure=
The crystal structure of tetraethylammonium iodide has been determined.E. Wait and H. M. Powell (1958). "The crystal and molecular structure of tetraethylammonium iodide." J. Chem. Soc. 1872-1875. The crystal structure is a distorted wurtzite lattice. At the nitrogen atom, the coordination is a flattened tetrahedron. The N−C−C angle is slightly larger than the tetrahedral angle.
=Synthetic applications=
Examples include:
- Stereoselective formation of (Z)-diiodoalkenes by treatment of alkynes with ICl in the presence of tetraethylammonium iodide.N. Hénaff and A. Whiting (2000). "Stereoselective formation of 1,2-diiodoalkenes and their application in the stereoselective synthesis of highly functionalised alkenes via Suzuki and Stille coupling reactions." J. Chem. Soc., Perkin 1 395-400.
- 2-Hydroxyethylation (attachment of −CH2−CH2−OH) by ethylene carbonate of carboxylic acids and certain heterocycles bearing an acidic N-H. For example, benzoic acid is converted to the ester, 2-hydroxyethyl benzoate, by treatment with ethylene carbonate in the presence of tetraethylammonium iodide.T.Yoshino et al. (1977). "Synthetic studies with carbonates. Part 6. Syntheses of 2-hydroxyethyl derivatives by reactions of ethylene carbonate with carboxylic acids or heterocycles in the presence of tetraethylammonium halides or under autocatalytic conditions." J. Chem. Soc., Perkin 1 1266-1272.
- Phase-transfer catalyst in geminal di-alkylation of fluorene, N,N-dialkylation of aniline and N-alkylation of carbazole using aqueous sodium hydroxide and alkyl halides.G. Saikia and P. K. Iyer (2010)."Facile C-H alkylation in water: enabling defect-free materials for optoelectronic devices." J. Org. Chem. 75 2714-2717.
Toxicity
LD50: 35 mg/kg (mouse, i.p.); 56 mg/kg (mouse, i.v.){{cite web | last=Brown | first=Jay A. | title=Tetraethylammonium iodide | website=Haz-Map | date=2019-05-13 | url=https://haz-map.com/Agents/19844 | access-date=2024-12-06}}