Chemistry:Tetrabutylammonium hydroxide

Tetrabutylammonium hydroxide

Names
Preferred IUPAC name N,N,N-Tributylbutan-1-aminium hydroxide
Other names TBAH, TBAOH
Identifiers
CAS Number	2052-49-5 Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL1078154 Y
ChemSpider	2005872 Y
PubChem CID	2723671
UNII	68I858J9S1 Y
InChI InChI=1S/C16H36N.H2O/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;/h5-16H2,1-4H3;1H2/q+1;/p-1 Y Key: VDZOOKBUILJEDG-UHFFFAOYSA-M Y InChI=1/C16H36N.H2O/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;/h5-16H2,1-4H3;1H2/q+1;/p-1 Key: VDZOOKBUILJEDG-REWHXWOFAE
SMILES [OH-].CCCC[N+](CCCC)(CCCC)CCCC
Properties
Chemical formula	C16H37NO
Molar mass	259.478 g·mol−1
Solubility in water	soluble
Solubility	soluble in most organic solvents
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

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 more conventional inorganic bases, such as KOH and NaOH, Bu₄NOH is more soluble in organic solvents.

Preparation and reactions

Solutions of Bu₄NOH are usually prepared in situ from butylammonium halides, Bu₄NX, for example by reacting them with silver oxide or using an ion exchange resin. Attempts to isolate Bu₄NOH induces Hofmann elimination, leading to Bu₃N and 1-butene. Solutions of Bu₄NOH are typically contaminated with Bu₃N for this reason.

Treatment of Bu₄NOH with a wide range of acids gives water and the other tetrabutylammonium salts: [math]\ce{ Bu4NOH + HX -> Bu4NX + H2O }[/math]

Applications

Bu₄NOH is a strong base that is used often under phase-transfer conditions to effect alkylations and deprotonations. Typical reactions include benzylation of amines and generation of dichlorocarbene from chloroform.

Bu₄NOH can be neutralized with a variety of mineral acids to give lipophilic salts of the conjugate base. For example, treatment of Bu₄NOH with disodium pyrophosphate, Na₂H₂P₂O₇, gives (Bu₄N)₃[HP₂O₇], which is soluble in organic solvents. Similarly, neutralization of Bu₄NOH with hydrofluoric acid affords an relatively water-free Bu₄NF. This salt dissolves in organic solvents and is useful in desilylation.