Tetrabutylammonium hydroxide 1484936 166926968 2007-10-25T06:27:35Z Daniel 1430004 Reverted edits by [[Special:Contributions/Ultradiablo|Ultradiablo]] ([[User talk:Ultradiablo|talk]]) to last version by Chem-awb {| align="right" width="300" border="1" cellspacing="0" cellpadding="3" style="margin: 0 0 0 0.5em; background: #FFFFFF; border-collapse: collapse" |- | align="center" colspan="2" | [[Image:TBAH.PNG|200px|TBAOH]] <br/> ''Tetrabutylammonium hydroxide'' |- | align="center" colspan="2" | '''[[IUPAC nomenclature|Chemical name]]''' <br/> Tetrabutylammonium hydroxide |- style="border-top: 3px solid gray" ! bgcolor="#ffddaa" colspan="2" | General |- | bgcolor="#ffeedd" | [[Chemical formula]] | C<sub>16</sub>H<sub>37</sub>NO |- | bgcolor="#ffeedd" | [[Molecular weight]] | 259.47 g/mol |- | bgcolor="#ffeedd" | Appearance | Colourless to light yellow solution |- | bgcolor="#ffeedd" | [[CAS number]] | 2052-49-5 |- | bgcolor="#ffeedd" | [[MSDS]] | [[Wikisource:Tetrabutylammonium hydroxide MSDS|Tetrabutylammonium hydroxide MSDS]] |- | bgcolor="#ffeedd" | [[SMILES]] | ? |- | bgcolor="#ffeedd" | Other names | TBAOH''' |- ! bgcolor="#ffddaa" colspan="2" | Physical properties |- | bgcolor="#ffeedd" | [[Solubility]] | [[water]], [[methanol]] |- | bgcolor="#ffeedd" | [[Density]] | 0.97 g/cm<sup>3</sup> (for solution 55% ''w''/''w'' at 20 °C) |- | bgcolor="#ffeedd" | [[pH]] (10% [[solution]] with [[water]]) | ? |- ! bgcolor="#ffddaa" colspan="2" | Phase behavior |- | bgcolor="#ffeedd" | [[Melting point]] | not obtainable as pure species |- | bgcolor="#ffeedd" | [[Boiling point]] | decomp |- ! bgcolor="#ffddaa" colspan="2" | Safety |- | bgcolor="#ffeedd" | Ingestion | Damage to the digestive tract. |- | bgcolor="#ffeedd" | Inhalation | burns to the respiratory tract. |- | bgcolor="#ffeedd" | Skin | burns. |- | bgcolor="#ffeedd" | Eyes | burns. |- ! bgcolor="#ffeedd" colspan="2" | Precautions |- | colspan="2" | * '''Hazards''': ** corrosive (class 8) * '''Personal protection''': |- style="border-top: 3px solid gray" ! bgcolor="#ffddaa" colspan="2" | [[Solid]] properties |- |'''Except where noted, all data was produced under conditions of [[standard temperature and pressure]].''' </small> |- |} Tetrabutyl ammonium hydroxide is the [[chemical compound]] with the formula (C<sub>4</sub>H<sub>9</sub>)<sub>4</sub>NOH, abbreviated Bu<sub>4</sub>NOH with the acronym TBAOH or TBAH. This species is not readily obtainable as a pure compound, but it employed as a solution in water or [[alcohol]]s. It is commonly used as a base in [[organic chemistry]]. Relative to more conventional inorganic bases, such as [[KOH]] and [[NaOH]], Bu<sub>4</sub>NOH is more soluble in organic solvents. Attempted isolation of pure Bu<sub>4</sub>NOH induces [[Hofmann elimination]], leading to Bu<sub>3</sub>N and [[1-butene]]. Solutions of Bu<sub>4</sub>NOH are typically contaminated with Bu<sub>3</sub>N for this reason.<ref>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.</ref> ==Applications in the synthesis of organic compounds== Bu<sub>4</sub>NOH is a strong base that is used often under [[phase transfer catalyst|phase-transfer]] conditions to effect [[alkylation]]s and [[deprotonation]]s. Typical reactions include [[benzyl]]ation of amines and generation of [[dichlorocarbene]] from [[chloroform]]. Bu<sub>4</sub>NOH can be [[Neutralization|neutralize]]d with a variety of [[mineral acid]]s to give lipophilic salts of the [[conjugate base]]. For example, treatment of Bu<sub>4</sub>NOH with [[disodium pyrophosphate]], Na<sub>2</sub>H<sub>2</sub>P<sub>2</sub>O<sub>7</sub>, gives (Bu<sub>4</sub>N)<sub>3</sub>[HP<sub>2</sub>O<sub>7</sub>], which is soluble in organic solvents.<ref>Woodside, A. B.; Huang, Z.; Poulter, C. D. “Trisammonium Geranyl Diphosphate” Organic Syntheses, Collected Volume 8, p.616 (1993). http://www.orgsyn.org/orgsyn/pdfs/CV8P0616.pdf</ref> Similarly, neutralization of Bu<sub>4</sub>NOH with [[hydrofluoric acid]] affords [[Tetra-n-butylammonium fluoride|Bu<sub>4</sub>NF]]. This salt dissolves in organic solvents and is useful to desilylation.<ref>Kuwajima, I.; Nakamura, E. Hashimoto, K. “Silylation of Ketones with Ethyl Trimethylsilacetate: (Z)-3-Trimethylsiloxy-2-Pentene” Organic Syntheses, Collected Volume 7, p.512 (1990). http://www.orgsyn.org/orgsyn/pdfs/CV7P0512.pdf</ref> ==Safety== Bu<sub>4</sub>NOH is toxic and corrosive. See MSDS. ==References== <references/> ==External links== [[Category:Quaternary ammonium compounds]] [[de:Tetrabutylammoniumhydroxid]]