| Revision as of 12:29, 10 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,074 edits Saving copy of the {{chembox}} taken from revid 453462475 of page Tetra-n-butylammonium_fluoride for the Chem/Drugbox validation project (updated: ''). |
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{{DISPLAYTITLE:Tetra-''n''-butylammonium fluoride}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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|Verifiedfields = changed |
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| verifiedrevid = 447872107 |
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|Watchedfields = changed |
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| Name = Tetra-''n''-butylammonium fluoride |
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|verifiedrevid = 470603123 |
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| ImageFile = TBAF.svg |
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|Name = Tetra-''n''-butylammonium fluoride |
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| ImageSize = 200px |
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|ImageFile = TBAF.svg |
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| ImageName = |
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|ImageSize = 150 |
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| IUPACName = Tetra-''n''-butylammonium fluoride |
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|PIN = ''N'',''N'',''N''-Tributylbutan-1-aminium fluoride |
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| Section1 = {{Chembox Identifiers |
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|OtherNames = Tetrabutylammonium fluoride; TBAF; ''n''-Bu<sub>4</sub>NF |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID = 2006300 |
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|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| PubChem = 2724141 |
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|ChemSpiderID = 2006300 |
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| InChI = 1/C16H36N.FH/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;/h5-16H2,1-4H3;1H/q+1;/p-1 |
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|PubChem = 2724141 |
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| InChIKey = FPGGTKZVZWFYPV-REWHXWOFAO |
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|InChI = 1/C16H36N.FH/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;/h5-16H2,1-4H3;1H/q+1;/p-1 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|InChIKey = FPGGTKZVZWFYPV-REWHXWOFAO |
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| StdInChI = 1S/C16H36N.FH/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;/h5-16H2,1-4H3;1H/q+1;/p-1 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChI = 1S/C16H36N.FH/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;/h5-16H2,1-4H3;1H/q+1;/p-1 |
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| StdInChIKey = FPGGTKZVZWFYPV-UHFFFAOYSA-M |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChIKey = FPGGTKZVZWFYPV-UHFFFAOYSA-M |
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| CASNo=429-41-4 |
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|CASNo_Ref = {{cascite|correct|CAS}} |
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| CASOther = <br /> (trihydrate) |
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|CASNo = 429-41-4 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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|CASNo2_Ref = {{cascite|changed|??}} |
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| ChEMBL = 1078233 |
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|CASNo2 = 87749-50-6 |
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| SMILES = .CCCC(CCCC)(CCCC)CCCC |
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|CASNo2_Comment = (trihydrate) |
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|UNII_Ref = {{fdacite|correct|FDA}} |
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|UNII = 2618F0C37I |
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|ChEMBL_Ref = {{ebicite|correct|EBI}} |
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|ChEMBL = 1078233 |
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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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| Formula = (C<sub>4</sub>H<sub>9</sub>)<sub>4</sub>N<sub></sub>F<sub></sub> |
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|Formula = (C<sub>4</sub>H<sub>9</sub>)<sub>4</sub>NF |
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| MolarMass = 261.46 g/mol |
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|MolarMass = 261.46 g/mol |
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|MeltingPtC = 58 to 60 |
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| Density = |
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| MeltingPt = 58-60 °C (trihydrate) |
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|MeltingPt_notes = (trihydrate) |
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'''Tetra-''n''-butylammonium fluoride''', commonly abbreviated to '''TBAF''' and '''''n''-Bu<sub>4</sub>NF''', is a ] with the chemical formula (CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>)<sub>4</sub>N<sup>+</sup>F<sup>−</sup>. It is commercially available as the white solid trihydrate and as a solution in ]. TBAF is used as a source of ] ion in organic solvents.<ref name="eEROS">{{cite book|editor-first=Leo A.|editor-last=Paquette|first1=Hui-Yin|last1=Li|first2=Haoran|last2=Sun|first3=Stephen G.|last3=DiMagno|title=]|chapter=Tetrabutylammonium Fluoride|date=2007|publisher=John Wiley & Sons|doi=10.1002/9780470842898.rt015.pub2|isbn=978-0471936237 }}</ref> |
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==Preparation and properties== |
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TBAF can be prepared by passing ] through an ], followed by ]. Upon evaporation of the water, TBAF can be collected as an oil in quantitative yield.<ref name="eEROS"/> |
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Preparing ] samples is of interest as the basicity of ] increases by more than 20 ] units on passing from aqueous to ].{{citation needed|date=January 2015}} However, heating samples of the hydrated material to 77 °C under vacuum causes decomposition to the ] salt.<ref name=sharma>{{cite journal |author1=Ramesh K. Sharma |author2=James L. Fry | title= Instability of anhydrous tetra-n-alkylammonium fluorides | journal= ] | year= 1983 | volume= 48 | pages= 2112–4 |doi=10.1021/jo00160a041 | issue= 12}}</ref> Similarly, samples dried at 40 °C under high vacuum still contain 10-30 mol% of water and some 10% of difluoride.<ref name=cox>{{cite journal |author1=D. Phillip Cox |author2=Jacek Terpinski |author3=Witold Lawrynowicz | title= 'Anhydrous' tetrabutylammonium fluoride: a mild but highly efficient source of nucleophilic fluoride ion | journal= ] | year= 1984 | volume= 49 | pages= 3216–9 |doi=10.1021/jo00191a035 | issue= 17}}</ref> Instead, anhydrous TBAF has been prepared by the reaction of ] and tetrabutylammonium cyanide. <!--Despite the considerable basicity of "naked" fluoride ion, in the absence of water, solutions of t-->Solutions of the salt in ] and ] are stable.<ref name=dimagno>{{cite journal |author1=Haoran Sun |author2=Stephen G. DiMagno |name-list-style=amp | title= Anhydrous Tetrabutylammonium Fluoride | journal= ] | year= 2005 | volume= 127 | pages= 2050–1| doi=10.1021/ja0440497 | pmid= 15713075 | issue= 7}}</ref> |
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==Reactions and uses== |
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Because the ] ion is such a strong ] acceptor, its salts tend to be hydrated and of limited ] in organic solvents. As a fluoride ion source, TBAF solves this problem, although the nature of the fluoride is uncertain because TBAF samples are almost always hydrated, resulting in the formation of bifluoride (HF<sub>2</sub><sup>−</sup>) hydroxide (OH<sup>−</sup>) as well as fluoride. Many applications tolerate heterogeneous or ill-defined fluoride sources. |
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As a fluoride source in organic solvents, TBAF is used to remove ] ]s. It is also used as a ] and as a mild ]. As a deprotecting agent, TBAF in DMSO will convert O-silylated enolates into carbonyls. With C-Si bonds, TBAF gives carbanions that can be trapped with electrophiles or undergo protonolysis.<ref name=eEROS/><ref>Nina Gommermann and Paul Knochel "N,N-Dibenzyl-N--amine from Cyclohexanecarbaldehyde, Trimethylsilylacetylene and Dibenzylamine" Org. Synth. 2007, 84, 1. {{doi|10.15227/orgsyn.084.0001}}</ref> |
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==References== |
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{{reflist}} |
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==Further reading== |
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* {{cite journal |author1=K. Hiroya |author2=R. Jouka |author3=M. Kameda |author4=A. Yasuhara |author5=T. Sakamoto |name-list-style=amp | title= Cyclization reactions of 2-alkynylbenzyl alcohol and 2-alkynylbenzylamine derivatives promoted by tetrabutylammonium fluoride | journal= ] | year= 2001| volume= 57| pages= 9697–710 |doi=10.1016/S0040-4020(01)00991-7 | issue= 48}}. |
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