Tetrabutylammonium hydroxide is the
chemical compound
A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...
with the formula (C
4H
9)
4NOH, abbreviated Bu
4NOH with the acronym TBAOH or TBAH. This species is employed as a solution in water or
alcohol
Alcohol most commonly refers to:
* Alcohol (chemistry), an organic compound in which a hydroxyl group is bound to a carbon atom
* Alcohol (drug), an intoxicant found in alcoholic drinks
Alcohol may also refer to:
Chemicals
* Ethanol, one of sev ...
s. It is a common base in
organic chemistry
Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, and reactions of organic compounds and organic materials, i.e., matter in its various forms that contain carbon atoms.Clayden, J.; ...
. Relative to more conventional inorganic bases, such as
KOH and
NaOH
Sodium hydroxide, also known as lye and caustic soda, is an inorganic compound with the formula NaOH. It is a white solid ionic compound consisting of sodium cations and hydroxide anions .
Sodium hydroxide is a highly caustic base and alkali ...
, Bu
4NOH is more soluble in organic solvents.
[.]
Preparation and reactions
Solutions of Bu
4NOH are usually prepared ''in situ'' from butylammonium halides, Bu
4NX, for example by reacting them with
silver oxide
Silver oxide is the chemical compound with the formula Ag2O. It is a fine black or dark brown powder that is used to prepare other silver compounds.
Preparation
Silver oxide can be prepared by combining aqueous solutions of silver nitrate and a ...
or using an
ion exchange resin
An ion-exchange resin or ion-exchange polymer is a resin or polymer that acts as a medium for ion exchange. It is an insoluble matrix (or support structure) normally in the form of small (0.25–1.43 mm radius) microbeads, usually white or ye ...
. Attempts to isolate Bu
4NOH induces
Hofmann elimination
Hofmann elimination is an elimination reaction of an amine to form alkenes. The least stable alkene (the one with the least number of substituents on the carbons of the double bond), called the Hofmann product, is formed. This tendency, known as ...
, leading to Bu
3N and
1-butene
1-Butene (or 1-Butylene) is the organic compound with the formula CH3CH2CH=CH2. It is a colorless gas that is easily condensed to give a colorless liquid. It is classified as a linear alpha-olefin. It is one of the isomers of butene (butylene). I ...
. Solutions of Bu
4NOH are typically contaminated with
Bu3N for this reason.
[
Treatment of Bu4NOH with a wide range of acids gives water and the other ]tetrabutylammonium
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 more ...
salts: Bu4NOH + HX -> Bu4NX + H2O
Applications
Bu4NOH is a strong base that is used often under phase-transfer conditions to effect alkylation
Alkylation is the transfer of an alkyl group from one molecule to another. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene (or their equivalents). Alkylating agents are reagents for effecting ...
s and deprotonation
Deprotonation (or dehydronation) is the removal (transfer) of a proton (or hydron, or hydrogen cation), (H+) from a Brønsted–Lowry acid in an acid–base reaction.Henry Jakubowski, Biochemistry Online Chapter 2A3, https://employees.csbsju.ed ...
s. Typical reactions include benzyl
In organic chemistry, benzyl is the substituent or molecular fragment possessing the structure . Benzyl features a benzene ring () attached to a methylene group () group.
Nomenclature
In IUPAC nomenclature, the prefix benzyl refers to a substi ...
ation of amines and generation of dichlorocarbene
Dichlorocarbene is the reactive intermediate with chemical formula CCl2. Although this chemical species has not been isolated, it is a common intermediate in organic chemistry, being generated from chloroform. This bent diamagnetic molecule rapidly ...
from chloroform
Chloroform, or trichloromethane, is an organic compound with chemical formula, formula Carbon, CHydrogen, HChlorine, Cl3 and a common organic solvent. It is a colorless, strong-smelling, dense liquid produced on a large scale as a precursor to ...
.[
Bu4NOH can be neutralized with a variety of ]mineral acid
A mineral acid (or inorganic acid) is an acid derived from one or more inorganic compounds, as opposed to organic acids which are acidic, organic compounds. All mineral acids form hydrogen ions and the conjugate base when dissolved in water.
Cha ...
s to give lipophilic salts of the conjugate base
A conjugate acid, within the Brønsted–Lowry acid–base theory, is a chemical compound formed when an acid donates a proton () to a base—in other words, it is a base with a hydrogen ion added to it, as in the reverse reaction it loses a ...
. For example, treatment of Bu4NOH with disodium pyrophosphate
Disodium pyrophosphate or sodium acid pyrophosphate (SAPP) is an inorganic compound consisting of sodium cations and pyrophosphate anion. It is a white, water-soluble solid that serves as a buffering and chelating agent, with many applications i ...
, Na2H2P2O7, gives (Bu4N)3 2O7">P2O7 which is soluble in organic solvents. Similarly, neutralization of Bu4NOH with hydrofluoric acid
Hydrofluoric acid is a Solution (chemistry), solution of hydrogen fluoride (HF) in water. Solutions of HF are colourless, acidic and highly Corrosive substance, corrosive. It is used to make most fluorine-containing compounds; examples include th ...
affords an relatively water-free Bu4NF. This salt dissolves in organic solvents and is useful to 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 ...
.[{{OrgSynth , authors = Kuwajima, I.; Nakamura, E.; Hashimoto, K. , title = Silylation of Ketones with Ethyl Trimethylsilacetate: (Z)-3-Trimethylsiloxy-2-Pentene , collvol = 7 , collvolpages = 512 , year = 1990 , prep = CV7P0512]
References
Tetrabutylammonium salts
Hydroxides