Tetraethylammonium iodide

Tetraethylammonium iodide
Names
	Preferred IUPAC name N,N,N-Triethylethanaminium iodide
	Other names Tetamon iodide; Tetramon J; TEAI
Identifiers
CAS Number	68-05-3;
3D model (JSmol)	Interactive image;
ChemSpider	5990;
ECHA InfoCard	100.000.615
PubChem CID	6225;
CompTox Dashboard (EPA)	DTXSID80883217 ;
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Properties
Chemical formula	C8H20IN
Molar mass	257.159 g·mol−1
Appearance	Colorless or yellowish crystalline solid
Density	1.566 g/cm3
Melting point	280 °C (536 °F; 553 K) (decomposes)
Solubility in water	soluble
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

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.^[2]

Structure[]

The crystal structure of tetraethylammonium iodide has been determined.^[3] 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.^[4]
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.^[5]
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.^[6]

Toxicity[]

LD₅₀: 35 mg/kg (mouse, i.p.); 56 mg/kg (mouse, i.v.)^{[citation needed]}

References[]

^ The Merck Index, 10th Ed., p.1316, Rahway: Merck & Co.
^ 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.
^ E. Wait and H. M. Powell (1958). "The crystal and molecular structure of tetraethylammonium iodide." J. Chem. Soc. 1872-1875.
^ 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.
^ 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.
^ 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.

[Merck-1] The Merck Index, 10th Ed., p.1316, Rahway: Merck & Co.

[2] 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.

[3] E. Wait and H. M. Powell (1958). "The crystal and molecular structure of tetraethylammonium iodide." J. Chem. Soc. 1872-1875.

[4] 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.

[5] 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.

[6] 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.

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