Tetrabutylammonium is a

quaternary ammonium cation In organic chemistry, quaternary ammonium cations, also known as quats, are positively-charged polyatomic ions of the structure , where R is an alkyl group, an aryl group or organyl group. Unlike the ammonium ion () and the primary, secondary, ...

with the formula , also denoted (where Bu =

butyl group In organic chemistry, butyl is a four-carbon alkyl radical or substituent group with general chemical formula , derived from either of the two isomers (''n''-butane and isobutane) of butane. The isomer ''n''-butane can connect in two ways, giv ...

). It is used in the research laboratory to prepare

lipophilic Lipophilicity (from Greek language, Greek λίπος "fat" and :wikt:φίλος, φίλος "friendly") is the ability of a chemical compound to dissolve in fats, oils, lipids, and non-polar solvents such as hexane or toluene. Such compounds are c ...

salts of inorganic anions. Relative to

tetraethylammonium Tetraethylammonium (TEA) is a quaternary ammonium cation with the chemical formula , consisting of four ethyl groups (, denoted Et) attached to a central nitrogen atom. It is a counterion used in the research laboratory to prepare lipophilic salt ...

derivatives, tetrabutylammonium salts are more lipophilic but

crystallize Crystallization is a process that leads to solids with highly organized atoms or molecules, i.e. a crystal. The ordered nature of a crystalline solid can be contrasted with amorphous solids in which atoms or molecules lack regular organization ...

less readily.

Derivatives

Some tetrabutylammonium salts of simple anions include: *

tetrabutylammonium fluoride Tetra-''n''-butylammonium fluoride, commonly abbreviated to TBAF and ''n''-Bu4NF, is a quaternary ammonium salt with the chemical formula (CH3CH2CH2CH2)4N+F−. It is commercially available as the white solid trihydrate and as a solution in tetra ...

, a

desilylation Silylation is the introduction of one or more (usually) substituted silyl groups (R3Si) to a molecule. Silylations are core methods for production of organosilicon chemistry. Silanization, while similar to silylation, usually refers to attachment ...

reagent. *

tetrabutylammonium bromide Tetrabutylammonium bromide (TBAB) is a quaternary ammonium salt with a bromide commonly used as a phase transfer catalyst. It is used to prepare many other tetrabutylammonium salts by salt metathesis reactions. The anhydrous form is a white soli ...

, a precursor to other tetrabutylammonium salts via

salt metathesis reaction A salt metathesis reaction (also called a double displacement reaction, double replacement reaction, or double decomposition) is a type of chemical reaction in which two ionic compounds in aqueous solution exchange their component ions to form two ...

s. * tetrabutylammonium iodide, a low cost catalyst. *

tetrabutylammonium triiodide Tetra-''n''-butylammonium triiodide (TBAI3) is a quaternary ammonium salt with a triiodide counterion. It is a common carrier of the triiodide used in chemical synthesis of photovoltaic materials, organic conductors and superconductors. In crysta ...

, a common carrier of the

triiodide In chemistry, triiodide usually refers to the triiodide ion, . This anion, one of the polyhalogen ions, is composed of three iodine atoms. It is formed by combining aqueous solutions of iodide salts and iodine. Some salts of the anion have been ...

anion used in chemical synthesis. *

tetrabutylammonium hydroxide Tetrabutylammonium hydroxide is a chemical compound with the formula (C4H9)4NOH, abbreviated Bu4NOH with the acronym TBAOH or TBAH. This species is employed as a solution in water or alcohols. It is a common base in organic chemistry. Relative to m ...

, a precursor to other tetrabutylammonium salts via acid-base reactions. *

tetrabutylammonium hexafluorophosphate Tetrabutylammonium hexafluorophosphate is a salt with the formula NBu4PF6. It is a white powder that is used as an electrolyte in nonaqueous electrochemistry. It is highly soluble in polar organic solvents such as acetone and acetonitrile. The sa ...

, an electrolyte for nonaqueous electrochemistry. Some tetrabutylammonium salts of more complex examples include: *

polyoxometalate In chemistry, a polyoxometalate (abbreviated POM) is a polyatomic ion, usually an anion, that consists of three or more transition metal oxyanions linked together by shared oxygen atoms to form closed 3-dimensional frameworks. The metal atoms are ...

s. *NS. * metal carbonyl anions. *Synthetic iron-sulfur clusters such as * Octachlorodirhenate ().{{cite book, first1=T. J. , last1=Barder, first2=R. A., last2=Walton, title=Inorganic Syntheses, chapter=Tetrabutylammonium Octachlorodirhenate(III), year=1990, volume=28, pages=332–334, doi=10.1002/9780470132593.ch83, isbn=9780470132593

References

Reagents for organic chemistry Quaternary ammonium compounds Cations

Derivatives

See also

References