Tetraethylammonium iodide

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.

Tetraethylammonium iodide
Names
Preferred IUPAC name
N,N,N-Triethylethanaminium iodide
Other names
Tetamon iodide; Tetramon J; TEAI
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.000.615
  • 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
  • [I-].CC[N+](CC)(CC)CC
Properties
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)
soluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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 NCC angle is slightly larger than the tetrahedral angle.

Synthetic applications

Examples include:

Toxicity

LD50: 35 mg/kg (mouse, i.p.); 56 mg/kg (mouse, i.v.)

See also

References

  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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