Tetrabutylammonium hydroxide

Tetrabutylammonium hydroxide

Names
IUPAC name tetrabutylammonium hydroxide
Identifiers
CAS Registry Number	2052-49-5 Y
ChEMBL	ChEMBL1078154 Y
ChemSpider	2005872 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
Jmol-3D images	Image
PubChem	2723671
SMILES [OH-].CCCC[N+](CCCC)(CCCC)CCCC
Properties
Molecular formula	C16H37NO
Molar mass	259.47 g·mol−1
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Y verify (what is: Y/N?)
Infobox references

Tetrabutylammonium hydroxide is the chemical compound with the formula (C₄H₉)₄NOH, abbreviated Bu₄NOH with the acronym TBAOH or TBAH. This species is not readily obtainable as a pure compound, but it is employed as a solution in water or alcohols. It is commonly used as a base in organic chemistry. Relative to more conventional inorganic bases, such as KOH and NaOH, Bu₄NOH is more soluble in organic solvents. Attempted isolation of pure Bu₄NOH induces Hofmann elimination, leading to Bu₃N and 1-butene. Solutions of Bu₄NOH are typically contaminated with Bu₃N for this reason.^[1]

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.^[2] Similarly, neutralization of Bu₄NOH with hydrofluoric acid affords Bu₄NF. This salt dissolves in organic solvents and is useful to desilylation.^[3]

References

1. ↑ Bos, M. E. "Tetra-n-butylammonium Hydroxide" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. doi:10.1002/047084289.
2. ↑ Woodside, A. B.; Huang, Z.; Poulter, C. D. (1993). "Trisammonium Geranyl Diphosphate". Org. Synth. ; Coll. Vol. 8, p. 616 
3. ↑ Kuwajima, I.; Nakamura, E. Hashimoto, K. (1990). "Silylation of Ketones with Ethyl Trimethylsilacetate: (Z)-3-Trimethylsiloxy-2-Pentene". Org. Synth. ; Coll. Vol. 7, p. 512