Tetrabutylammonium

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.

Tetrabutylammonium

Names
Preferred IUPAC name N,N,N-Tributylbutan-1-aminium
Other names Tetrabutylammonium Tetrabutylazanium
Identifiers
CAS Number	10549-76-5 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:45825
ChEMBL	ChEMBL1236196
ChemSpider	15220
DrugBank	DB01851
PubChem CID	16028
UNII	CBU2X6BBJR
CompTox Dashboard (EPA)	DTXSID3045011
InChI InChI=1S/C16H36N/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4/h5-16H2,1-4H3/q+1 Y Key: DZLFLBLQUQXARW-UHFFFAOYSA-N
SMILES CCCC[N+](CCCC)(CCCC)CCCC
Properties
Chemical formula	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). Infobox references

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

• N-Butyllithium

References

1. Shi, Erbo; Shao, Ying; Chen, Shulin; Hu, Huayou; Liu, Zhaojun; Zhang, Jie; Wan, Xiaobing (2012-07-06). "Tetrabutylammonium Iodide Catalyzed Synthesis of Allylic Ester with tert-Butyl Hydroperoxide as an Oxidant". Organic Letters. 14 (13): 3384–3387. doi:10.1021/ol3013606. ISSN 1523-7060. PMID 22731787.
2. Klemperer, W. G. (1990). "Tetrabutylammonium Isopolyoxometalates". Inorganic Syntheses. Vol. 27. pp. 74–85. doi:10.1002/9780470132586.ch15. ISBN 9780470132586.
3. Bojes, J.; Chivers, T.; Drummond, I. (1978). "Heptathiazocine(Heptasulfurimide) and Tetrabutylammonium Tetrathionitrate". Inorganic Syntheses. Vol. 18. pp. 203–206. doi:10.1002/9780470132494.ch36. ISBN 9780470132494.
4. Ceriotti, A.; Longoni, G.; Marchionna, M. (1989). "Bis(Tetrabutylammonium) Hexa-μ-Carbonyl-Hexacarbonylhexaplatinate(2 -), [N(C ₄ H ₉ ) ₄ ] ₂ [Pt ₆ (Co) ₆ (μ-Co) ₆ ]". Inorganic Syntheses. Vol. 26. pp. 316–319. doi:10.1002/9780470132579.ch57. ISBN 978-0-471-50485-6.
5. Christou, George; Garner, C. David; Balasubramaniam, A.; Ridge, Brian; Rydon, H. N. (1982). "9. Tetranuclear Iron-Sulfur and Iron-Selenium Clusters". Tetranuclear Iron-Sulfur and Iron-Selenium Clusters. Inorganic Syntheses. Vol. 21. pp. 33–37. doi:10.1002/9780470132524.ch9. ISBN 9780470132524..
6. Barder, T. J.; Walton, R. A. (1990). "Tetrabutylammonium Octachlorodirhenate(III)". Inorganic Syntheses. Vol. 28. pp. 332–334. doi:10.1002/9780470132593.ch83. ISBN 9780470132593.