- Tetrabutylammonium hydroxide
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IUPACName=tetrabutylammonium hydroxide
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Section1=Chembox Identifiers
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PubChem=2723671
SMILES=CCCC [N+] (CCCC)(CCCC)CCCC. [OH-]
Section2=Chembox Properties
C=16 | H=37 | N=1 | O=1
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Section3=Chembox Hazards
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Autoignition=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 employed as a solution in water oralcohol s. It is commonly used as a base inorganic chemistry . Relative to more conventional inorganic bases, such asKOH andNaOH , Bu4NOH is more soluble in organic solvents. Attempted isolation of pure Bu4NOH inducesHofmann elimination , leading to Bu3N and1-butene . Solutions of Bu4NOH are typically contaminated with Bu3N for this reason. [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.]Applications
Bu4NOH is a strong base that is used often under phase-transfer conditions to effect
alkylation s anddeprotonation s. Typical reactions includebenzyl ation of amines and generation ofdichlorocarbene fromchloroform .Bu4NOH can be neutralized with a variety of
mineral acid s to give lipophilic salts of theconjugate base . For example, treatment of Bu4NOH withdisodium pyrophosphate , Na2H2P2O7, gives (Bu4N)3 [HP2O7] , which is soluble in organic solvents. [OrgSynth | author = Woodside, A. B.; Huang, Z.; Poulter, C. D. | title = Trisammonium Geranyl Diphosphate | collvol = 8 | collvolpages = 616 | year = 1993 | prep = cv8p0616] Similarly, neutralization of Bu4NOH withhydrofluoric acid affords Bu4NF. This salt dissolves in organic solvents and is useful to desilylation. [OrgSynth | author = 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
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