Tetrabutylammonium is a
quaternary ammonium cation
In chemistry, quaternary ammonium cations, also known as quats, are positively charged polyatomic ions of the structure , R being an alkyl group or an aryl group. Unlike the ammonium ion () and the primary, secondary, or tertiary ammonium cations ...
with the formula
(C4H9)4sup>+. It is used in the research laboratory to prepare lipophilic salts of inorganic anions. Relative to
tetraethylammonium
Tetraethylammonium (TEA), () or (Et4N+) is a quaternary ammonium cation consisting of four ethyl groups attached to a central nitrogen atom, and is positively charged. It is a counterion used in the research laboratory to prepare lipophilic salts ...
derivatives, tetrabutylammonium salts are more lipophilic but crystallize 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+Fâ. 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. The process is the basis of organosilicon chemistry.
Of organic compounds
Alcohols, carboxylic acids, amines, thiols, and phosphates can be sily ...
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, sometimes called a double displacement reaction, is a chemical process involving the exchange of bonds between two reacting chemical species which results in the creation of products with similar or identical bonding a ...
s.
*
tetrabutylammonium iodide
Tetrabutylammonium is a quaternary ammonium cation with the formula (C4H9)4sup>+. It is used in the research laboratory to prepare lipophilic salts of inorganic anions. Relative to tetraethylammonium derivatives, tetrabutylammonium salts are mor ...
, 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 bee ...
anion used in chemical synthesis.
*
tetrabutylammonium hydroxide
Tetrabutylammonium hydroxide is the 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 ...
, 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 s ...
, 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
e4S4(SPh)4sup>2â
*
Octachlorodirhenate (
e2Cl8sup>2â).
[{{cite book, first1=T. J. , last1=Barder, first2=R. A., last2=Walton, title=Inorganic Syntheses, series=Inorganic Syntheses, chapter=Tetrabutylammonium Octachlorodirhenate(III), year=1990, volume=28, page=332â334, doi=10.1002/9780470132593.ch83, isbn=9780470132593]
See also
*
N-Butyllithium
''n''-Butyllithium C4H9Li (abbreviated ''n''-BuLi) is an organolithium reagent. It is widely used as a polymerization initiator in the production of elastomers such as polybutadiene or styrene-butadiene-styrene (SBS). Also, it is broadly emp ...
References
Reagents for organic chemistry
Quaternary ammonium compounds
Cations