Tetrabutylammonium is a quaternary ammonium cation with the formula [N(C4H9)4]+, also denoted [NBu4]+ (where Bu = butyl group). It is used in the research laboratory to prepare lipophilic salts of inorganic anions. Relative to tetraethylammonium derivatives, tetrabutylammonium salts are more lipophilic but crystallize less readily.
Names | |
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Preferred IUPAC name N,N,N-Tributylbutan-1-aminium | |
Other names Tetrabutylammonium Tetrabutylazanium | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChEMBL | |
ChemSpider | |
DrugBank | |
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CompTox Dashboard (EPA) | |
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Properties | |
C16H36N+ | |
Molar mass | 242.470 g·mol−1 |
Related compounds | |
Related compounds | tetrabutylammonium fluoride tetrabutylammonium bromide tetrabutylammonium hydroxide tetrabutylammonium hydroxide tetrabutylammonium hexafluorophosphate |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Derivatives
Some tetrabutylammonium salts of simple anions include:
- tetrabutylammonium fluoride, a desilylation reagent.
- tetrabutylammonium bromide, a precursor to other tetrabutylammonium salts via salt metathesis reactions.
- tetrabutylammonium iodide, a low cost catalyst.[1]
- tetrabutylammonium triiodide, a common carrier of the triiodide anion used in chemical synthesis.
- tetrabutylammonium hydroxide, a precursor to other tetrabutylammonium salts via acid-base reactions.
- tetrabutylammonium hexafluorophosphate, an electrolyte for nonaqueous electrochemistry.
Some tetrabutylammonium salts of more complex examples include:
- polyoxometalates.[2]
- NS−
4.[3] - metal carbonyl anions.[4]
- Synthetic iron-sulfur clusters such as [Fe4S4(SPh)4]2−[5]
- Octachlorodirhenate ([Re2Cl8]2−).[6]
See also
References
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