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{{chembox |
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{{chembox |
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| verifiedrevid = 402681959 |
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| verifiedrevid = 470603420 |
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|ImageFile=TBAH.PNG |
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| ImageFile = TBAH.PNG |
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|ImageSize= |
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| ImageSize = |
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| PIN = ''N'',''N'',''N''-Tributylbutan-1-aminium hydroxide |
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|IUPACName=tetrabutylammonium hydroxide |
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|OtherNames= |
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| OtherNames = TBAH, TBAOH |
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|Section1={{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 2005872 |
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| ChemSpiderID = 2005872 |
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| 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 |
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| 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 |
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| StdInChIKey = VDZOOKBUILJEDG-UHFFFAOYSA-M |
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| StdInChIKey = VDZOOKBUILJEDG-UHFFFAOYSA-M |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo=2052-49-5 |
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| CASNo = 2052-49-5 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| PubChem=2723671 |
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| ChEMBL = 1078154 |
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| UNII = 68I858J9S1 |
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| PubChem = 2723671 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 1078154 |
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| SMILES = .CCCC(CCCC)(CCCC)CCCC |
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| SMILES = .CCCC(CCCC)(CCCC)CCCC |
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|Section2={{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=16 | H=37 | N=1 | O=1 |
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| C=16 | H=37 | N=1 | O=1 |
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| Solubility= soluble |
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| SolubleOther = soluble in most organic solvents |
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|Section3={{Chembox Hazards |
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|Section3={{Chembox Hazards |
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'''Tetrabutylammonium hydroxide''' is the ] 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 ]s. It is commonly used as a base in ]. Relative to more conventional inorganic bases, such as ] and ], Bu<sub>4</sub>NOH is more soluble in organic solvents. Attempted isolation of pure Bu<sub>4</sub>NOH induces ], leading to Bu<sub>3</sub>N and ]. 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> |
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'''Tetrabutylammonium hydroxide''' is the ] 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 employed as a solution in water or ]s. It is a common base in ]. Relative to more conventional inorganic bases, such as ] and ], Bu<sub>4</sub>NOH is more soluble in organic solvents.<ref name=eEROS>{{cite book|last=Bos|first=Mary Ellen|chapter=Tetrabutylammonium Hydroxide|title=Encyclopedia of Reagents for Organic Synthesis|editor-last=Paquette|editor-first=Leo A.|year=2004|publisher=J. Wiley & Sons|location=New York|doi=10.1002/047084289X.rt017|isbn=0-471-93623-5 }}.</ref> |
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==Preparation and reactions== |
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Solutions of Bu<sub>4</sub>NOH are usually prepared ''in situ'' from butylammonium halides, Bu<sub>4</sub>NX, for example by reacting them with ] or using an ]. Attempts to isolate Bu<sub>4</sub>NOH induces ], leading to Bu<sub>3</sub>N and ]. Solutions of Bu<sub>4</sub>NOH are typically contaminated with ] for this reason.<ref name=eEROS/> |
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Treatment of Bu<sub>4</sub>NOH with a wide range of acids gives water and the other ] salts: <chem>Bu4NOH + HX -> Bu4NX + H2O</chem> |
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==Applications== |
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==Applications== |
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Bu<sub>4</sub>NOH is a strong base that is used often under ] conditions to effect ]s and ]s. Typical reactions include ]ation of amines and generation of ] from ]. |
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Bu<sub>4</sub>NOH is a strong base that is used often under ] conditions to effect ]s and ]s. Typical reactions include ]ation of amines and generation of ] from ].<ref name=eEROS/> |
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Bu<sub>4</sub>NOH can be ]d with a variety of ]s to give lipophilic salts of the ]. For example, treatment of Bu<sub>4</sub>NOH with ], 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>, which is soluble in organic solvents.<ref>{{OrgSynth | author = Woodside, A. B.; Huang, Z.; Poulter, C. D. | title = Trisammonium Geranyl Diphosphate | collvol = 8 | collvolpages = 616 | year = 1993 | prep = cv8p0616}}</ref> Similarly, neutralization of Bu<sub>4</sub>NOH with ] affords ]. This salt dissolves in organic solvents and is useful to ].<ref>{{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}}</ref> |
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Bu<sub>4</sub>NOH can be ]d with a variety of ]s to give lipophilic salts of the ]. For example, treatment of Bu<sub>4</sub>NOH with ], 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>, which is soluble in organic solvents.<ref>{{OrgSynth |author=Woodside, A. B. |author2=Huang, Z. |author3=Poulter, C. D. | title = Trisammonium Geranyl Diphosphate | collvol = 8 | collvolpages = 616 | year = 1993 | prep = cv8p0616}}</ref> Similarly, neutralization of Bu<sub>4</sub>NOH with ] affords a relatively water-free ]. This salt dissolves in organic solvents and is useful in ].<ref>{{OrgSynth |author=Kuwajima, I. |author2=Nakamura, E. |author3=Hashimoto, K. | title = Silylation of Ketones with Ethyl Trimethylsilacetate: (Z)-3-Trimethylsiloxy-2-Pentene | collvol = 7 | collvolpages = 512 | year = 1990 | prep = CV7P0512}}</ref> |
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==References== |
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==References== |
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