38932-80-8

Usage

Uses

1. Organic Synthesis:
Tetrabutylammonium tribromide is used as a phase transfer catalyst in organic synthesis, facilitating a wide range of reactions and leading to good yields with low catalyst loading. It is particularly useful for preparing O-isopropylidene derivatives from sugars and their derivatives at room temperature.
2. Mild Brominating Agent:
TBATB serves as a mild brominating agent, enabling the preparation of vicinal dibromides from alkenes and alkynes, as well as alfa-bromo acetals.
3. HBr Generation:
It is utilized to generate hydrogen bromide (HBr), which acts as an efficient chemoselective reagent for the acetalization of carbonyl compounds.
4. Antimicrobial Agents Synthesis:
Tetrabutylammonium tribromide is employed in the synthesis of antimicrobial agents, specifically through the synthesis of chalcones.
5. Tubulin Polymerization Inhibitors:
TBATB is also used in the synthesis of potent tubulin polymerization inhibitors, which have potential applications in the development of new therapeutics.
6. Reagent in Organic Synthesis:
As a reagent, TBATB is a conveniently weighable, solid source of bromine, making it a valuable component in various organic synthesis processes.

InChI:InChI=1/C16H36N.Br3/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;1-3-2/h5-16H2,1-4H3;/q+1;-1

Upstream product

• 1643-19-2 tetrabutylammomium bromide 
• 109-65-9 1-bromo-butane 
• 102-82-9 tributyl-amine 

Downstream Products

• 501334-28-7 (E)-3-(3-bromo-4-hydroxyphenyl)-2-cyano-N-nonyl-2-butenamide 
• 62179-79-7 2-bromo-1-(4-(pentyloxy)phenyl)ethan-1-one 
• 1643-19-2 tetrabutylammomium bromide 
• 1361257-64-8 trans-1-bromo-1,2-difluorohexene 
• 429-42-5 tetrabutylammonium tetrafluoroborate 

Relevant academic research and scientific papers

Polybromide salts of tetraalkyl and N-heterocyclic cations: New entries into the structural library

Reactions between Br2 dissolved in HBr and salts of various organic cations resulted in formation of a series of polyhalide salts: (IsoquinolH)Br3 (1), (2-BrPyH)Br3 (2), (H2(4,4′-bipy))(Br3)2 (3), Bu4NBr3 (4), (Collidinium){(Br3)(Br2)} (5) and Et4N{(Br3)(Br2)2} (6). All compounds were characterized by X-ray diffractometry; the role of supramolecular Br?Br contacts is discussed.

Controlling Stereoselectivity in Tribromide Mediated Oxidative Dearomatisations – Synthesis of Selective Spirofurano-naphthalones

A series of ammonium tribromides were screened for exploring the role of ammonium counterpart attached to tribromides on generation of stereoselective spiro-furans via oxidative dearomatisation of naphthols. The proposition enlightens a suitable combination of the ammonium tribromide and solvent employed, deliver the best achieved diastereoselectivities. This in turn, has also envisioned the mechanistic aspects related to this category of reactions. The mentioned dearomative spiro-furano naphthalones has also been successfully achieved on a large-scale.

A Photorobust Mo(0) Complex Mimicking [Os(2,2′-bipyridine)3]2+and Its Application in Red-to-Blue Upconversion

Osmium(II) polypyridines are a well-known class of complexes with luminescent metal-to-ligand charge-transfer (MLCT) excited states that are currently experiencing a revival due to their application potential in organic photoredox catalysis, triplet-triplet annihilation upconversion, and phototherapy. At the same time, there is increased interest in the development of photoactive complexes made from Earth-abundant rather than precious metals. Against this background, we present a homoleptic Mo(0) complex with a new diisocyanide ligand exhibiting different bite angles and a greater extent of π-conjugation than previously reported related chelates. This new design leads to deep red emission, which is unprecedented for homoleptic arylisocyanide complexes of group 6 metals. With a 3MLCT lifetime of 56 ns, an emission band maximum at 720 nm, and a photoluminescence quantum yield of 1.5% in deaerated toluene at room temperature, the photophysical properties are reminiscent of the prototypical [Os(2,2′-bipyridine)3]2+ complex. Under 635 nm irradiation with a cw-laser, the new Mo(0) complex sensitizes triplet-triplet annihilation upconversion of 9,10-diphenylanthracene (DPA), resulting in delayed blue fluorescence with an anti-Stokes shift of 0.93 eV. The photorobustness of the Mo(0) complex and the upconversion quantum yield are high enough to generate a flux of upconverted light that can serve as a sufficiently potent irradiation source for a blue-light-driven photoisomerization reaction. These findings are relevant in the greater contexts of designing new luminophores and photosensitizers for use in red-light-driven photocatalysis, photochemical upconversion, light-harvesting, and phototherapy.

Tetrabutylammonium tribromide: An effective green reagent for the one-pot reaction of 3-acetyl-2H-chromen-2-ones with o-phenylenediamines

An efficient and completely greener approach has been outlined for the reaction of 3-acetyl-2H-chromen-2-ones with o-phenylenediamines using tetrabutylammonium tribromide (TBATB) to obtain 3-(quinoxalin-2-yl)-2H-chromen-2-ones in one-pot. Alternatively, a step-wise method has also been demonstrated for the synthesis of 3-(quinoxalin-2-yl)-2H-chromen-2-ones, where 3-acetyl-2H-chromen-2-ones has first treated with TBATB to give 3-(2-bromoacetyl)-2H-chromen-2-one followed by its nucleophilic substitution reaction with o-phenylenediamines. Use of polyethylene glycol-600 (PEG-600) as the solvent media, mild reaction conditions and easy isolation procedure of products are the added advantages for this synthesis. Both the one-pot and step-wise methods have been compared in terms of their reaction yields and one-pot synthesis was found to be superior. All the synthesized compounds were confirmed by characterization with 1HNMR, 13CNMR, HRMS, IR spectroscopy.

Process Development of the HCV NS5B Site D Inhibitor MK-8876

We describe the route development and multikilogram-scale synthesis of an HCV NS5B site D inhibitor, MK-8876. The key topics covered are (1) process improvement of the two main fragments; (2) optimization of the initially troublesome penultimate step, a key bis(boronic acid) (BBA)-based borylation; (3) process development of the final Suzuki-Miyaura coupling; and (4) control of the drug substance form. These efforts culminated in a 28 kg delivery of the desired active pharmaceutical ingredient.

On the bromination of aromatics, alkenes and alkynes using alkylammonium bromide: Towards the mimic of bromoperoxidases reactivity

This article describes an efficient method of bromination of organic substrates including aromatics, alkenes and alkynes with NH4VO3as a catalyst and H2O2as an oxidant agent using a non-toxic and easy-to-handle source of bromine, tetrabutylammonium bromide. The process was developed under mild reaction conditions and is an innovation from reported methods in aspects such as: i) short reaction times, ii) the ability to work at room temperature, iii) regioselectivity and good yields.

Novel Metal- and Mineral-Acid-Free Synthesis of Organic Ammonium Tribromides and Application of Ethylenephenanthrolium Bistribromide for Bromination of Active Methylene Group of 1,3-Diketones and β-Ketoesters

A novel procedure for the preparation of organic ammonium tribromides (OATBs) is described from their corresponding bromides. Quaternary ammonium bromides (QABs) and a N,N′-heterocyclic dibromide are efficiently oxidized to their corresponding monotribromides and bistribromide by m-chloroperbenzoic acid (MCPBA) in the presence of 2 and 4 equiv of KBr, respectively. The reactions are carried out in an aqueous medium without the use of any mineral acid or metal catalyst/promoters. A variety of tribromides are synthesized in very good yields including a hitherto unknown reagent, 1,10-(ethane-1, 2-diyl)phenanthrolinediium bistribromide (EPDBT). EPDBT is investigated as brominating agent and found to be highly effective for selective bromination of active methylene groups of a variety of 1,3-diketones and β-ketoesters. GRAPHICAL ABSTRACT.

Sodium hypochlorite-promoted novel synthesis of organic ammonium tribromides and application of phenanthroline hydrotribromide in chemoselective oxidation of organic sulfides by hydrogen peroxide

A novel method of synthesis of organic ammonium tribromides (OATBs) is developed by using an inexpensive and eco-friendly sodium hypochlorite as oxidant for conversion of Br to Br3 . The OATBs thus prepared include both quaternary ammonium tribromides and N-heterocyclic tribromides. A new addition to the family of OATBs is made in the form of phenanthroline hydrotribromide. The efficacy of this new tribromide as catalyst is ascertained in the oxidative transformation of organic sulfides to their corresponding sulfoxides and sulfones by hydrogen peroxide.

Novel protocol for the synthesis of organic ammonium tribromides and investigation of 1,1′-(Ethane-1,2-diyl)dipiperidinium bis(tribromide) in the silylation of alcohols and thiols

A novel and efficient protocol for the synthesis of organic ammonium tribromides (OATBs) is developed by using inexpensive and eco-friendly periodic acid as an oxidant for the conversion of Br-to Br3-. The method does not use any mineral acid and metal oxidants. The protocol is utilized to synthesize a new bis(tribromide) viz., 1,1′-(ethane-1,2-diyl)dipiperidinium bis(tribromide) (EDPBT). EDPBT is investigated as a catalyst in the silylation of alcohols and thiols by HMDS (hexamethyldisilazane) under solvent-free conditions.

Novel method of synthesis of quaternary ammonium tribromides and investigation of catalytic role of benzyltrimethylammonium tribromide in oxidation of alcohols to carbonyl compounds

Stable crystalline organic quaternary ammonium tribromides (QATBs) have been easily synthesized by the oxidation of the corresponding organic ammonium bromides (QABs) with ammonium persulfate. The reactions have been performed under solvent-free conditions in the presence of sulfuric acid and silica as supporting agent. Two equivalents of potassium bromide have been used as the source of additional bromides for quantitative conversion of QABs to QATBs.Ammonium persulfate, a cheap and readily available oxidant, carries out the bromide oxidation to tribromide very effectively under solvent-free conditions. The synthesized QATBs have been shown to catalyze the oxidation of alcohols to carbonyl compounds with hydrogen peroxide as oxidant in good yields under mild reaction conditions. Copyright Taylor & Francis Group, LLC.