13826-83-0 Purity
99%+
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Specification
Tetrabutylammonium bromide (TBAB) has emerged as a valuable additive in Sonogashira coupling, specifically facilitating the palladium/copper-catalyzed reaction of N-tosyl aryltriazenes to produce arylalkynes. In this role, TBAB serves as a dual activator, effectively increasing the efficiency of both the palladium catalyst and the aryltriazene substrates, resulting in yields up to 92%.
In the TBAB-promoted Sonogashira coupling process, TBAB enables the oxidative addition of palladium(0) directly to aryltriazenes without the need for in situ aryl halide formation, thereby streamlining the catalytic cycle. The unique activation provided by TBAB supports the selective conversion of N-tosyl aryltriazenes into arylalkynes, while maintaining compatibility with a variety of functional groups. However, some electronic variations in alkyne substrates can impact the reaction's efficiency, necessitating careful selection of reagents for optimal outcomes.
This TBAB-assisted methodology holds notable advantages over traditional Sonogashira couplings, where TBAB's activation properties enhance both reaction efficiency and yield, as well as reaction scope by tolerating a range of functional groups.
Tetrabutylammonium bromide (TBABr) has emerged as a crucial additive in the development of hydrated deep eutectic solvent (HDES) electrolytes for zinc-bromine batteries, addressing significant challenges in battery performance. Stationary zinc-bromine batteries are recognized as a promising energy solution, yet their commercialization has been hindered by the instability of zinc metal at the anode and the problematic cross-diffusion of bromine at the cathode.
In this innovative approach, TBABr serves a dual function. At the anode, it stabilizes zinc metal by forming a protective layer, thereby enhancing cycling stability. Concurrently, at the cathode, TBABr mitigates bromine cross-diffusion by forming solid complexes with bromine species (Br₃⁻), reducing the adverse effects of this diffusion on overall battery efficiency.
To optimize the solubility and effectiveness of TBABr, the composition of the HDES was systematically fine-tuned. This included adjustments to the zinc-to-halide ratio, variations in water content, and the incorporation of ethylene glycol, resulting in a significant improvement in electrolyte performance. The optimized electrolyte enabled the zinc anode to cycle stably for over 3300 hours at a current density of 0.5 mA/cm², and in a full-cell configuration, the battery achieved a remarkable specific capacity of 297 mAh/g. Notably, the cell maintained stability over 11,500 cycles with an impressive 99.9% coulombic efficiency. These findings underscore the critical role of TBABr in enhancing the performance and longevity of zinc-bromine batteries, marking it as a significant advancement in the pursuit of reliable, next-generation energy storage solutions.
Tetrabutylammonium bromide (TBAB) has been identified as a significant enhancer of ice nucleation in aqueous systems, addressing challenges related to the dispersion of traditional nucleation promoters. In studies focused on improving ice formation, TBAB was found to facilitate the effective dispersion of AgI, kaolinite, and cholesterol in liquid water, which are otherwise difficult to integrate into aqueous phases.
The experimental setup involved preparing various concentrations of TBAB solutions and dispersing nucleation promoters at a fixed ratio of 2.5 wt%. Notably, TBAB alone was shown to unexpectedly promote ice nucleation, suggesting that its presence influences the nucleation kinetics beyond mere dispersion. When AgI was added to 1 mM TBAB solutions, a further enhancement in ice nucleation rates was observed, underscoring TBAB's role in optimizing the effectiveness of AgI as a nucleation promoter.
However, the dispersion of kaolinite and cholesterol did not yield a significant increase in nucleation rates compared to TBAB solutions without these additives. This outcome indicates that while TBAB is effective in improving the stability and distribution of certain nucleation promoters, its intrinsic properties may overshadow the contributions of others.
The research highlights the critical importance of TBAB in stabilizing nucleation promoter suspensions, enabling precise control over ice nucleation processes. As such, TBAB emerges as a vital component in studies of ice formation, with implications for understanding climate phenomena and enhancing technologies that rely on ice nucleation, such as weather modification and cryopreservation. These findings affirm TBAB's multifaceted role in facilitating ice nucleation, providing a foundation for further investigations into its mechanisms and applications in various fields.
Tetrabutylammonium bromide (TBAB) has been investigated for its role in the formation of deep eutectic solvents (DESs) in combination with imidazole and choline chloride. This study focuses on the structural characterization and interaction dynamics within these eutectic mixtures, leveraging various analytical techniques such as vibrational spectroscopy and X-ray diffraction.
The TBABr-imidazole eutectic mixture is prepared by combining TBAB in a molar ratio of 3:7 with imidazole, heating the mixture to 80°C to achieve a homogeneous colorless liquid. Subsequent drying under vacuum at 70°C yields a stable DES. This innovative combination capitalizes on the hydrogen bonding interactions among TBAB, imidazole, and choline chloride, resulting in a significant depression of melting points compared to the individual components.
Detailed analysis through infrared and Raman spectroscopy reveals insights into the microscopic distribution of the components within the solvent. The vibrational spectra indicate strong intermolecular interactions, highlighting the synergistic effects of TBAB in enhancing the solvation properties of imidazole. X-ray diffraction studies further elucidate the structural organization of the solvent mixture, confirming the presence of specific intermolecular contacts that govern the unique characteristics of the DES.
Computational studies complement these findings, providing molecular dynamics simulations and quantum chemistry calculations that reinforce the experimental observations. The results elucidate the nature of interactions between anions, cations, and imidazole, establishing TBAB as a crucial component in the development of efficient DESs.
This study explores the use of Tetrabutylammonium bromide (N 444 Br) as a hydrogen bond acceptor (HBA) in a deep eutectic solvent (DES) system for the extraction of dihydromyricetin (DMY) from vine tea. A DES-oscillating solvent extraction (DES-OS) process combined with macroporous resin adsorption-desorption was employed to achieve a green and efficient method for isolating this flavonoid. DMY, a bioactive compound with notable antioxidant properties, is challenging to extract due to its polar structure, making the solvent choice critical to yield and purity.
Preparation of DES System: Tetrabutylammonium bromide (N 444 Br) served as the HBA, paired with pyruvic acid (HBD) in a 1:2 molar ratio to create a homogeneous DES. The preparation followed a simple heating and stirring method, wherein N 444 Br and HBD were mixed and stirred at 80°C until a stable liquid formed. This liquid DES was left overnight at 30°C to stabilize further.
DMY Extraction from Vine Tea: To optimize extraction conditions, 1 g of dried vine tea powder was mixed with 10 mL of DES at 30°C and shaken at 200 rpm for 3 hours. Following extraction, samples were centrifuged at 10,000 rpm for 10 minutes, after which the supernatant was diluted and analyzed via HPLC.
Optimization Results: Through single-factor experiments and Box-Behnken design (BBD) response surface methodology, key parameters-water content, extraction time, and temperature-were optimized. The final conditions yielded a high extraction rate of 40.1 mg·g⁻¹ of DMY at 71.18% DES water content, 2.8 hours extraction time, and 46.4°C, closely aligning with predicted values.
In recent studies, tetrabutylammonium bromide (TBAB) has demonstrated its catalytic enhancement abilities within cobalt Prussian blue analogue (CoCo-PBA) systems, as well as its use as a hydrogen bond acceptor in deep eutectic solvents (DES).
In catalytic applications, TBAB-modified CoCo-PBA serves as an efficient and stable heterogeneous catalyst for coupling CO₂ with epoxides to form cyclic carbonates under mild conditions (1.0 MPa, 65°C), achieving >99% yield. The unique structure of CoCo-PBA, combined with TBAB's catalytic assistance, provides enhanced surface activity and stability, addressing the need for sustainable CO₂ conversion methods with low energy requirements. This catalyst also demonstrates broad applicability, maintaining 98% activity after six cycles and performing well with various industrial-grade epoxides, highlighting the flexibility of the TBAB-modified CoCo-PBA catalytic system.
Additionally, TBAB has shown its versatility in DES systems designed for the efficient extraction of bioactive compounds. When used as a hydrogen bond acceptor with pyruvic acid, TBAB enables the creation of a stable, biocompatible DES that facilitates the selective extraction of dihydromyricetin (DMY) from vine tea. Through optimized conditions, DES containing TBAB achieves a high DMY extraction rate of 40.1 mg·g⁻¹, offering a green alternative to conventional extraction solvents.
This study presents a simple, novel method for preparing monodisperse submicron silica particles via a TBABr-assisted Stöber process. By increasing the concentration of tetrabutylammonium bromide (TBABr) in the reaction medium from 0 to 20.0 mM, the resulting silica particle size increased from 0.39 to 1.08 μm, with a polydispersity of less than 5%. The presence of TBABr effectively suppressed the condensation rate of silanol monomers during the Stöber reaction, slowing the formation of silica seeds and thereby promoting the growth of larger silica particles.
The preparation method for the silica particles is as follows: Typically, a mixture containing 0.40 mL H₂O, 2.25 mL NH₃·H₂O, and a specified volume of ethanol is combined with 0.4 mL of TEOS and an appropriate volume of 0.4 M TBABr in ethanol. As the volume of TBABr solution is gradually increased from 0 to 0.25, 0.50, 0.75, and 1.00 mL, the volume of ethanol is adjusted accordingly from 19.60 to 19.35, 19.10, 18.85, and 18.60 mL to maintain a constant total reaction volume of 22.65 mL. This adjustment results in a TBABr concentration range from 0 to 5.0, 10.0, 15.0, and 20.0 mM. After stirring at 20 °C for 6 hours, the particles are purified by repeated centrifugation (5000 rpm, 10 minutes), removing the supernatant and redistributing the particles in ethanol for further characterization.
The molecular formula of Tetrabutylammonium Bromide is C16H36BrN.
The molecular weight of Tetrabutylammonium Bromide is 322.37 g/mol.
Some synonyms for Tetrabutylammonium Bromide are Tetra-N-butylammonium bromide and Tetrabutyl ammonium bromide.
The IUPAC name of Tetrabutylammonium Bromide is tetrabutylazanium;bromide.
The Canonical SMILES representation of Tetrabutylammonium Bromide is CCCC[N+](CCCC)(CCCC)CCCC.[Br-].
The CAS number for Tetrabutylammonium Bromide is 1643-19-2.
The InChIKey for Tetrabutylammonium Bromide is JRMUNVKIHCOMHV-UHFFFAOYSA-M.
Tetrabutylammonium Bromide has 1 hydrogen bond acceptor.
Tetrabutylammonium Bromide has 12 rotatable bonds.
The topological polar surface area of Tetrabutylammonium Bromide is 0-2.
Some synonyms for Tetrabutylammonium Bromide include Tetra-N-butylammonium bromide, Tetrabutyl ammonium bromide, and TBAB.
Tetrabutylammonium Bromide was first created on 2005-03-27.
There is 1 hydrogen bond acceptor in Tetrabutylammonium Bromide.
The exact mass of Tetrabutylammonium Bromide is 321.20311 g/mol.
There are 12 rotatable bond counts in Tetrabutylammonium Bromide.
Reference: [1] Patent: EP1580189, 2005, A1, . Location in patent: Page/Page column 32
Reference: [1] Chemische Berichte, 1981, vol. 114, # 9, p. 3004 - 3018
Reference: [1] Journal of Physical Chemistry B, 2012, vol. 116, # 15, p. 4561 - 4574
Reference: [1]Synthetic Communications,1989,vol. 19,p. 1309 - 1316
Reference: [1]Journal of the Chemical Society, Faraday Transactions 1: Physical Chemistry in Condensed Phases,1987,vol. 83,p. 1879 - 1884
Reference: [1]Patent: WO2004/54962,2004,A1 .Location in patent: Page 10
* For details of the synthesis route, please refer to the original source to ensure accuracy.