429-41-4

Usage

Uses

Used in Organic Synthesis:
Tetrabutylammonium fluoride is used as a catalyst for etherification of alcohols and phenols with alkyl halides, as well as for benzylation reactions. It facilitates the formation of ether and benzyl ether compounds, which are important in the synthesis of various organic compounds.
Used in Condensation, Cyclization, Fluorination, and Desulfonylation Reactions:
TBAF is employed as a reagent in organic syntheses for condensation, base-catalyzed cyclization reactions, fluorination, and desulfonylation reactions. Its ability to act as a base and a fluoride source makes it a valuable component in these processes.
Used as a Deprotecting Agent:
Tetrabutylammonium fluoride is used as a deprotecting agent in organic synthesis, where it helps remove protecting groups from functional groups, allowing further reactions to occur.
Used in Fluoride Sensor Development:
In the research field of fluoride sensor development, TBAF is used as an easy-to-handle and measurable fluoride anion source. The fluoride in TBAF, once dissolved, can be considered a free fluoride with little interaction with the ammonium cation, making it suitable for monitoring sensing reactions with visible spectroscopy.
Used as a Base, Phase Transfer Catalyst, and Fluoride Source:
Tetrabutylammonium fluoride (TBAF) is commonly used in organic chemistry as a base, a phase transfer catalyst, and as a fluoride source. Its solubility in organic solvents and its ability to transfer fluoride ions make it a valuable tool in various chemical reactions.

InChI:InChI=1/C16H36N.FH.3H2O/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;;;;/h5-16H2,1-4H3;1H;3*1H2/q+1;;;;/p-1

Upstream product

• 1643-19-2 tetrabutylammomium bromide 
• 1112-67-0 tetrabutyl-ammonium chloride 
• 32503-27-8 tetra(n-butyl)ammonium hydrogensulfate 
• 193819-24-8 tetrabutylammonium hydrogen bifluoride 
• 10442-39-4 tetra-n-butylammonium cyanide 
• 1897-50-3 5-chloro-2,4,6-trifluoroisophthalonitrile 
• 392-56-3 Hexafluorobenzene 
• 1186217-08-2 C₁₆H₃₆N⁽¹⁺⁾*C₇₂H₇₂N₄O₉*F^(1-) 
• 10534-59-5 tetrabutylammonium acetate 
• 429-42-5 tetrabutylammonium tetrafluoroborate 

Downstream Products

• 1126-80-3 (n-butylthio)benzene 
• 13153-10-1 1-(butylsulfinyl)benzene 
• 112-53-8 1-dodecyl alcohol 
• 334-68-9 1-fluorododecane 
• 74-85-1 ethene 
• 17739-53-6 di-phenylmethylsilyl fluoride 
• 99892-99-6 C₁₆H₃₆N⁽¹⁺⁾*C₁₁H₁₀N₃O₅^(1-) 
• 700-58-3 2-Adamantanone 
• 111756-00-4 tetrabutylammonium m-carbomethoxyphenolate 
• 111756-01-5 tetra-n-butylammonium salt of methyl 6-hydroxy-2-naphthoate 
• 120414-30-4 5-Carbamoyl-2-oxo-cyclohexanecarboxylic acid methyl ester 
• 120414-33-7 3-(2,6-Dioxo-piperidin-3-yl)-butyric acid methyl ester 
• 120414-32-6 (2R,3R)-3-Carbamoyl-2-methyl-6-oxo-cyclohexanecarboxylic acid methyl ester 
• 104013-65-2 Tetrabutylammonium 4-cyanophenate 

Relevant academic research and scientific papers

Low-temperature NMR spectra of fluoride-acetic acid hydrogen-bonded complexes in aprotic polar environment

Using low-temperature NMR (1H, 19F) technique in the slow exchange regime, the solutions containing tetrabutylammonium (TBA) acetate and HF have been studied in an aprotic freon mixture, CDF3/CDF 2Cl, exhibiting a dielectric permittivity, which increases strongly by lowering the temperature. Two different hydrogen bonded anionic clusters, a 1:1 cluster of the type AcOδ-?H?F -1+δ+ ([AcOHF]-) and a 2:1 cluster of the type AcOH?F-?HOAc ([(AcOH)2F]-) have been detected in equilibrium with each other, both forming ion pairs with the TBA countercation. [AcOHF]- exhibits an extremely strong hydrogen bond, with a proton shared between partially negatively charged oxygen and fluorine atoms. The NMR chemical shifts and scalar spin-spin coupling constants, 1J(FH), have been measured in the temperature range between 110 and 160 K, where separate NMR signals are observed for both species. In addition, H/D isotope effects on the 19F NMR chemical shielding have been measured for both clusters. In contrast to the related complexes [(FH) nF]- (n=1-4) studied previously, the NMR parameters of [AcOHF]- and of [(AcOH)2F]- depend strongly on temperature. This effect is associated with the increasing polarity of the solvent with decreasing temperatures, established earlier, which displaces the proton from fluorine to oxygen. As a motive power of this conversion, preferential solvation of the compact fluoride ion as compared to acetate is proposed.

Convenient Procedures for the Preparation of Lipophilic Quaternary Onium Fluorides, Hydrogendifluorides and Dihydrogentrifluorides via Ion Exchange in Two-Phase Systems

A series of lipophilic quaternary onium fluorides 2, hydrogendifluorides 3, and dihydrogentrifluorides 4 are easily synthesized in almost quantitative yields from the corresponding quaternary hydrogen sulfates by exchange with the appropriate anion in an organic aqueous two-phase system; alternatively quaternary salts 4 can be prepared from onium chlorides 5 or bromides 6 under the same conditions.

Boron-Containing Organic Diradicaloids: Dynamically Modulating Singlet Diradical Character by Lewis Acid-Base Coordination

Organic diradicaloids have unique open-shell structures and properties and promising applications in organic electronics and spintronics. Incorporation of heteroatoms is an effective strategy to alter the electronic structures of organic diradicaloids. However, B-containing organic diradicaloids are very challenging due to their high reactivities, which are caused by not only diradical nature but also the B atom. In this article, we report a new kind of organic diradicaloids containing boron atoms. Our strategy is to incorporate planarized triarylboranes to antiaromatic polycyclic hydrocarbons (PHs). We synthesized two isomeric B-containing PHs composed of indenofluorene π-skeletons and two dioxa-bridged triphenylborane moieties. As proved by theoretical and experimental results, both of them have excellent ambient stability and open-shell singlet diradical structures, as well as intriguing magnetic and optoelectronic properties, such as thermally accessible triplet species, reversible multiredox ability, and narrow energy gaps. Notably, they possess sufficient Lewis acidity, which has never been observed for organic diradicaloids. In addition, they can coordinate with Lewis bases to form Lewis adducts, achieving unprecedented dynamic modulations of (anti)aromaticity and thus diradical character of organic diradicaloids.

Unraveling the cation and anion effects and kinetics for ionic liquid catalyzed direct synthesis of methyl acrylate under mild conditions

The direct synthesis of methyl acrylate (MA) from methyl acetate and trioxane at 350-380 °C is regarded as a supplementary route for the industrial propylene oxidation process; however, it suffers from rapid catalyst deactivation. Herein, a novel ionic liquid catalyzed mild liquid-phase system was developed for the direct synthesis of MA from methyl acetate and trioxane, where N,O-bis(trimethylsilyl)acetamide (BSA) was used as a probase for α-deprotonation and enol silyl etherification of methyl acetate. The trioxane decomposition to formaldehyde and methyl acetate enolization to 1-methoxy-1-trimethylsilyloxyethene proceeded with the catalysis of [Cation]Cl/MClx (M = Cu+, Fe3+, Zn2+ and Al3+) and [Cation]F, respectively. The cations and anions were observed to have significant effects on the yield and selectivity of MA, owing to the steric hindrance, acid site category and strength confirmed by pyridine probing FT-IR characterization. As a result, up to 60.2% yield with 94.6% selectivity of MA could be achieved when [N3,3,3,3]F and [N3,3,3,3]Cl/AlCl3 with 67 mol% AlCl3 were used in the presence of BSA at 25 °C. Kinetic studies indicated that the trioxane decomposition with the activation barrier of 41.2 ± 0.3 kJ mol-1 was the rate-determining step.

Syntheses and anion binding capabilities of bis(diarylboryl) ferrocenes and related systems

Isomeric diborylated ferrocenes featuring 1,1′-, 1,2-, and 1,3-substitution patterns have been targeted via a combination of electrophilic aromatic substitution and directed ortho-lithiation protocols. While none of these systems are competent for the Lewis acid chelation of fluoride, related systems featuring a mixed B/Si acceptor set capture 1 equiv of fluoride via a Si-F-B bridging motif.

A naked eye detection of fluoride with urea receptors which have both an azo group and a nitrophenyl group as a signaling group

Anion recognition via hydrogen-bonding interactions could be monitored with changes in UV-vis absorption spectra and in some cases easily monitored with naked eye. Urea receptors 1 and 2 connected with both an azo group and a nitrophenyl group as a signaling group for color change proved to be an efficient naked eye receptor for the fluoride ion. The anion recognition phenomena of the receptors 1 and 2 via hydrogen-bonding interactions were investigated through UV-vis absorption and 1H NMR spectra.

Encapsulated binding sites - Synthetically simple receptors for the binding and transport of HCl

We report a receptor with an encapsulated amine/amide binding site, which binds HCl with high affinity in organic media - the rate of HCl transport through an apolar phase is controlled by the degree of encapsulation of the HCl binding site.

Methods and Agents for Preparing 18F-Radiolabeled Fluorinating Agents

The present invention is directed to a method for preparing an anhydrous 18F-radiolabeled fluorinating agent by a nucleophilic reaction of a hydrated 18F-radiolabeled fluoride ion source with an unsaturated carrier compound; treating the 18F-radiolabeled carrier compound to produce a non-aqueous mixture of the 18F-radiolabeled carrier compound in a solvent; and reacting the 18F-radiolabeled carrier compound with a nucleophilic composition in a nucleophilic reaction to produce an anhydrous 18F-radiolabeled fluorinating agent. The present invention is also directed to an anhydrous 18F-radiolabeled fluorinating agent comprising the formula [QnM]x+(18F?)x. Additionally, the present invention is directed to an 18F-radiolabeled fluorinated radiopharmaceutical or an 18F-radiolabeled fluorinated radiotracer prepared by reacting the anhydrous 18F-radiolabeled fluorinating agent with a drug intermediate. The present invention is further directed to methods for treating a disease or imaging a subject using an 18F-radiolabeled fluorinated radiopharmaceutical or an 18F-radiolabeled fluorinated radiotracer.

Fluoride relay: A new concept for the rapid preparation of anhydrous nucleophilic fluoride salts from KF

Fluoride relay is used to generate exceptionally nucleophilic fluoride reagents from KF on a time scale commensurate with radiotracer synthesis. The Royal Society of Chemistry.

Anhydrous flouride salts and reagents and methods for their production

Anhydrous organic fluoride salts and reagents prepared by a method comprising the nucleophilic substitution of a fluorinated aromatic or fluorinated unsaturated organic compound with a salt having the formula: [QnM]x+Ax?in an inert polar, aprotic solvent; wherein M is an atom capable of supporting a formal positive charge, the n groups Q are independently varied organic moieties, n is an integer such that the [QnM] carries at least one formal positive charge, x is an integer defining the number of formal positive charge(s), +, carried by the [QnM], A? is an anionic nucleophile capable of substituting for F in the fluorinated compound and F represents fluorine or a radioisotope thereof.