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Tetrabutylammonium hydroxide information


Tetrabutylammonium hydroxide
Names
Preferred IUPAC name
N,N,N-Tributylbutan-1-aminium hydroxide
Other names
TBAH, TBAOH
Identifiers
CAS Number
  • 2052-49-5 checkY
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL1078154 checkY
ChemSpider
  • 2005872 checkY
ECHA InfoCard 100.016.498 Edit this at Wikidata
PubChem CID
  • 2723671
UNII
  • 68I858J9S1 checkY
CompTox Dashboard (EPA)
  • DTXSID8062155 Edit this at Wikidata
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 checkY
    Key: VDZOOKBUILJEDG-UHFFFAOYSA-M checkY
  • 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
SMILES
  • [OH-].CCCC[N+](CCCC)(CCCC)CCCC
Properties
Chemical formula
C16H37NO
Molar mass 259.478 g·mol−1
Solubility in water
soluble
Solubility soluble in most organic solvents
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒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 employed as a solution in water or alcohols. It is a common base in organic chemistry. Relative to more conventional inorganic bases, such as KOH and NaOH, Bu4NOH is more soluble in organic solvents.[1]

  1. ^ Bos, Mary Ellen (2004). "Tetrabutylammonium Hydroxide". In Paquette, Leo A. (ed.). Encyclopedia of Reagents for Organic Synthesis. New York: J. Wiley & Sons. doi:10.1002/047084289X.rt017. ISBN 0-471-93623-5..

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Tetrabutylammonium hydroxide

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Tetrabutylammonium hydroxide is the chemical compound with the formula (C4H9)4NOH, abbreviated Bu4NOH with the acronym TBAOH or TBAH. This species is employed...

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Tetrabutylammonium

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cost catalyst. tetrabutylammonium triiodide, a common carrier of the triiodide anion used in chemical synthesis. tetrabutylammonium hydroxide, a precursor...

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Tetrabutylammonium bromide

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Tetrabutylammonium bromide (TBAB) is a quaternary ammonium salt with a bromide commonly used as a phase transfer catalyst. It is used to prepare many other...

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Organic base

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organic bases, such as tetramethylammonium hydroxide, tetrabutylammonium hydroxide, or choline hydroxide are hydroxide donors rather than proton acceptors like...

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Quaternary ammonium cation

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indicated by the stability of the hydroxide salts such as tetramethylammonium hydroxide and tetrabutylammonium hydroxide even at elevated temperatures. The...

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MXenes

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delaminated into single and few layers by immersing the MXene in tetrabutylammonium hydroxide, followed by sonication. MXenes can also be synthesized directly...

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Fluoride

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salts of naked fluoride include tetramethylammonium fluoride and tetrabutylammonium fluoride. Cobaltocenium fluoride is another example. However, they...

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Salt metathesis reaction

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of sodium perrhenate to the tetrabutylammonium salt: NaReO4 + N(C4H9)4Cl → N(C4H9)4[ReO4] + NaCl The tetrabutylammonium salt precipitates from the aqueous...

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Tetramethylammonium fluoride

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also known. Anhydrous Tetrabutylammonium fluoride has been prepared by the reaction of hexafluorobenzene and tetrabutylammonium cyanide. Iashin, Vladimir;...

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Bromobenzenes

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and triphenylphosphine (PPh 3), tetrabutylammonium iodide (TBAI) as a phase-transfer catalyst, and sodium hydroxide as a base. Below is an example reaction...

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Orthosilicic acid

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The acid was crystallized from a solution of dimethylacetamide and tetrabutylammonium chloride. As established by X-ray crystallography, the chloride anions...

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Sodium orthovanadate

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orthovanadate is produced by dissolving vanadium(V) oxide in a solution of sodium hydroxide: V2O5 + 6 NaOH → 2 Na3VO4 + 3 H2O The salt features tetrahedral VO3−4...

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Ester

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Synthesis of Esters from Carboxylic Acids and Alkyl Halides Using Tetrabutylammonium Fluoride". Journal of Oleo Science. 63 (5): 539–544. doi:10.5650/jos...

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Williamson ether synthesis

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facile. Finally, phase transfer catalysts are sometimes used (e.g. tetrabutylammonium bromide or 18-crown-6) in order to increase the solubility of the...

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Tetraethylammonium

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prepare lipophilic salts of inorganic anions. It is used similarly to tetrabutylammonium, the difference being that its salts are less lipophilic, more easily...

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Electrosynthesis

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dichloromethane with electrolytes such as lithium perchlorate or tetrabutylammonium salts. The choice of electrodes with respect to their composition...

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Dichlorocarbene

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aqueous sodium hydroxide. A phase transfer catalyst, for instance benzyltriethylammonium bromide, facilitates the migration of the hydroxide in the organic...

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Trifluoromethylation

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example is the trifluoromethylation of cyclohexanone in THF using tetrabutylammonium fluoride. The substrates can be aryl halides. Potassium...

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Diallyl disulfide

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synthesized from the same starting materials, but in air and using tetrabutylammonium bromide as a catalyst. The corresponding yield is below 82%. The major...

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Tetrapropylammonium

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The halide salts are then converted to the more industrially valuable hydroxide by reaction with aqueous silver oxide, electrolysis, ion-exchange resin...

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Caesium chloride

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0^{\circ }C}}]{ArCH=N-C(C2H4COOCH3)(CH3)-COOC(CH3)3}}}} where TBAB is tetrabutylammonium bromide (interphase catalyst) and CPME is a cyclopentyl methyl ether...

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Rhenium compounds

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perrhenic acid. Addition of tetrabutylammonium chloride to aqueous solutions of sodium perrhenate gives tetrabutylammonium perrhenate, which is soluble...

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Protecting group

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hydrofluoric acid in acetonitrile, pyridinium fluoride in tetrahydrofuran, tetrabutylammonium fluoride in THF. Commonly protects 2'-hydroxy function in oligonucleotide...

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Polyoxometalate

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polyoxometalates. As the pH is lowered, orthometalates protonate to give oxide–hydroxide compounds such as WO3(OH)− and VO3(OH)2−. These species condense via the...

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