Tetrabutylammonium

Tetrabutylammonium
Names
	Preferred IUPAC name Tetrabutylazanium
	Other names Tetrabutylammonium; N,N,N-tributylbutan-1-aminium
Identifiers
CAS Number	2052-49-5 ;
	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 ;
Properties
Chemical formula	C16H36N
Molar mass	242.471 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

Tetrabutylammonium is a quaternary ammonium cation with the formula [N(C₄H₉)₄]⁺. 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.

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 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.[1]
NS⁻
₄.[2]
metal carbonyl anions.[3]
Synthetic iron-sulfur clusters such as [Fe₄S₄(SPh)₄]²⁻[4]
Octachlorodirhenate ([Re₂Cl₈]²⁻).[5]

References

Klemperer, W. G. (1990). "Tetrabutylammonium Isopolyoxometalates". Inorganic Syntheses. Inorganic Syntheses. 27. p. 74–85. doi:10.1002/9780470132586.ch15. ISBN 9780470132586.
Bojes, J.; Chivers, T.; Drummond, I. (1978). "Heptathiazocine(Heptasulfurimide) and Tetrabutylammonium Tetrathionitrate". Inorganic Syntheses. Inorganic Syntheses. 18. p. 203–206. doi:10.1002/9780470132494.ch36. ISBN 9780470132494.
Ceriotti, A.; Longoni, G.; Marchionna, M. (1989). Bis(Tetrabutylammonium) Hexa-μ-Carbonyl-Hexacarbonylhexaplatinate(2−), [N(C₄H₉)₄]₂[Pt₆(CO)₆(μ-CO)₆]. Inorganic Syntheses. 26. p. 316–319. doi:10.1002/9780470132579.ch57.
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. 21. p. 33–37. doi:10.1002/9780470132524.ch9. ISBN 9780470132524..
Barder, T. J.; Walton, R. A. (1990). "Tetrabutylammonium Octachlorodirhenate(III)". Inorganic Syntheses. Inorganic Syntheses. 28. p. 332–334. doi:10.1002/9780470132593.ch83. ISBN 9780470132593.

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[1] Klemperer, W. G. (1990). "Tetrabutylammonium Isopolyoxometalates". Inorganic Syntheses. Inorganic Syntheses. 27. p. 74–85. doi:10.1002/9780470132586.ch15. ISBN 9780470132586.

[2] Bojes, J.; Chivers, T.; Drummond, I. (1978). "Heptathiazocine(Heptasulfurimide) and Tetrabutylammonium Tetrathionitrate". Inorganic Syntheses. Inorganic Syntheses. 18. p. 203–206. doi:10.1002/9780470132494.ch36. ISBN 9780470132494.

[3] Ceriotti, A.; Longoni, G.; Marchionna, M. (1989). Bis(Tetrabutylammonium) Hexa-μ-Carbonyl-Hexacarbonylhexaplatinate(2−), [N(C₄H₉)₄]₂[Pt₆(CO)₆(μ-CO)₆]. Inorganic Syntheses. 26. p. 316–319. doi:10.1002/9780470132579.ch57.

[4] 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. 21. p. 33–37. doi:10.1002/9780470132524.ch9. ISBN 9780470132524..

[5] Barder, T. J.; Walton, R. A. (1990). "Tetrabutylammonium Octachlorodirhenate(III)". Inorganic Syntheses. Inorganic Syntheses. 28. p. 332–334. doi:10.1002/9780470132593.ch83. ISBN 9780470132593.