Tetraethylammonium iodide

Tetraethylammonium iodide
Names
	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 ;
	InChI InChI=1S/C8H20N.HI/c1-5-9(6-2,7-3)8-4;/h5-8H2,1-4H3;1H/q+1;/p-1 Key: UQFSVBXCNGCBBW-UHFFFAOYSA-M; InChI=1/C8H20N.ClH/c1-5-9(6-2,7-3)8-4;/h5-8H2,1-4H3;1H/q+1;/p-1 Key: UQFSVBXCNGCBBW-UHFFFAOYSA-M;
	SMILES [I-].CC[N+](CC)(CC)CC;
Properties
Chemical formula	C8H20IN
Molar mass	257.159 g·mol−1
Appearance	Colorless or yellowish crystalline solid
Density	1.566 g/cm3[1]
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.)

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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.

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[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.