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tetrabutylammonium
Sign in to saveAlso known as tetra-n-butylammonium, tetrabutyl ammonium
Tetrabutylammonium is a quaternary ammonium cation with the formula , also denoted (where Bu = butyl group). It is used in the research laboratory to prepare lipophilic salts of inorganic anions. Relative to tetraethylammonium derivatives, tetrabutylammonium salts are more lipophilic but crystallize less readily. It is useful for phase-transfer catalysis.
In the Vinony graph
Within Vinony's link graph, tetrabutylammonium is referenced by 30 other articles, and connects out to International Standard Book Number, digital object identifier and International Standard Serial Number.
It is catalogued under topics including Cations, Quaternary ammonium compounds and Reagents for organic chemistry.
Its subject is documented across 4 Wikipedia language editions.
Chemical data
- Formula
- C16H36N+
- Molecular weight
- 242.46 g/mol
- IUPAC name
- tetrabutylazanium
- SMILES
- CCCC[N+](CCCC)(CCCC)CCCC
- InChIKey
- DZLFLBLQUQXARW-UHFFFAOYSA-N
- XLogP
- 5.3
- Polar surface area
- 0 Ų
- H-bond donors
- 0
- H-bond acceptors
- 0
- Formal charge
- 1
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
3,266 papers- Tetrabutylammonium Bromide (TBAB) Catalyzed Synthesis of Bioactive Heterocycles.Molecules (Basel, Switzerland) · 2020
- Synthetic utility of biomimicking vanadium bromoperoxidase and n-tetrabutylammonium tribromide (TBATB) in organic synthesis.Organic & biomolecular chemistry · 2022
- Tetrabutylammonium HPLC analysis: shortcomings in the Ph. Eur. method.Journal of labelled compounds & radiopharmaceuticals · 2020
- Anhydrous tetrabutylammonium fluoride.Journal of the American Chemical Society · 2005
- Tetrabutylammonium Chloride-Induced Cascade Radical Addition/Cyclization of O-Isocyanodiaryl Amines: A Novel Protocol for the Synthesis of 11-Trifluoromethylated Dibenzodiazepines.The Journal of organic chemistry · 2022
via PubMed
Wikidata facts
Show 3 more facts
- canonical SMILES
- CCCC[N+](CCCC)(CCCC)CCCC
- chemical formula
- C₁₆H₃₆N⁺
- Commons category
- Tetrabutylammonium cation
Sources (1)
via Wikidata · CC0
~1 min read
Encyclopedic overview
3 sectionsContents
- Derivatives
- See also
- References
Tetrabutylammonium is a quaternary ammonium cation with the formula , also denoted (where Bu = butyl group). It is used in the research laboratory to prepare lipophilic salts of inorganic anions. Relative to tetraethylammonium derivatives, tetrabutylammonium salts are more lipophilic but crystallize less readily. It is useful for phase-transfer catalysis.
==Derivatives== Some tetrabutylammonium salts of simple anions include: tetrabutylammonium fluoride, a desilylation reagent. tetrabutylammonium bromide, a precursor to other tetrabutylammonium salts via salt metathesis reactions. tetrabutylammonium iodide, a low cost catalyst. tetrabutylammonium triiodide, a common carrier of the triiodide anion used in chemical synthesis. tetrabutylammonium hydroxide, a precursor to other tetrabutylammonium salts via acid-base reactions. tetrabutylammonium hexafluorophosphate, an electrolyte for nonaqueous electrochemistry. Some tetrabutylammonium salts of more complex examples include: polyoxometalates. NS. metal carbonyl anions. Synthetic iron-sulfur clusters such as Octachlorodirhenate ().
Excerpted from Wikipedia’s “tetrabutylammonium” article, available under the CC BY-SA 4.0 licence.