Tetraethylammonium iodide

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Tetraethylammonium iodide
Tetraethylammonium iodide.svg
Identifiers
CAS number 68-05-3
PubChem 6225
ChemSpider 5990
Jmol-3D images Image 1
Properties
Molecular formula C8H20IN
Molar mass 257.16 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 noted otherwise, 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 (see "Chemistry" section).

Chemistry[edit]

Preparation[edit]

Tetraethylammonium iodide is commercially available, but can be prepared by the reaction between triethylamine and ethyl iodide.[2]

Structure[edit]

The crystal structure of tetraethylammonium iodide has been determined.[3]

Synthetic Applications[edit]

Examples include:

Toxicity[edit]

LD50: 35 mg/kg (mouse, i.p.); 56 mg/kg (mouse, i.v.)[7]

See also[edit]

References[edit]

  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.
  7. ^ http://www.drugfuture.com/toxic/q10-q780.html