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Basic Information of Tetrabutylammonium Tribromide:
Common Names: Tetrabutylammonium tribromide, TBATB
CAS NO: 38932-80-8
Chromatographic Purity: ≥99.0%
Molecular Formula: C₁₆H₃₆NBr₃
Molecular Weight: 482.18
Melting Point: 71-76 °C (lit.)
Density: 1.5469 (rough estimate)
Uses: This product is primarily used as a brominating reagent and catalyst. In organic synthesis, it selectively brominates phenols, aromatic amines, acetylaromatic amines, methyl ketones, alkenes, alkynes, alcohols, and related compounds.
tetrabutylammonium bromide (TBATB) is a versatile and efficient quaternary ammonium salt, widely recognized as a superior brominating reagent and catalyst in modern organic synthesis. Composed of a tetrabutylammonium cation and a tribromide anion, it excels in selectively introducing bromine into various substrates, including phenols, aromatic amines, enolizable ketones, alkenes, alkynes, and alcohols. Its excellent stability, high reactivity, and good solubility make it a reagent of choice for both laboratory research and industrial-scale production.
Key Features & Advantages
High Stability: Exhibits excellent thermal stability at room temperature, ensuring safe, long-term storage and easy handling.
Superior Reactivity & Selectivity: Serves as a potent source of bromine, facilitating rapid and selective bromination reactions with high yields and purity.
Excellent Solubility: Readily soluble in common organic solvents (e.g., DCM, acetonitrile, THF), promoting homogeneous reaction conditions and simplifying process optimization.
Broad Applicability: A versatile tool for diverse transformations such as bromine addition, cyclization, bromine transfer, and catalytic cycles.
Synthesis Methods
TBATB can be reliably produced through several established methods:
Direct Bromination: Reaction of tetrabutylammonium bromide with elemental bromine under controlled conditions.
Ion Exchange: A mild and scalable approach involving ion-exchange techniques to form the tribromide salt.
Multi-step Synthesis: For applications requiring ultra-high purity, controlled multi-step processes including crystallization can be employed.
Primary Applications
1. Organic Synthesis
TBATB is fundamental for constructing complex molecular architectures. It efficiently installs bromine atoms, a crucial functional handle, in the synthesis of pharmaceuticals, agrochemicals, natural products, and functional materials.
2. Catalysis
Acts as an effective catalyst or co-catalyst in various reactions, including halogenation and cross-coupling processes. It enhances reaction rates and selectivity, aligning with the principles of efficient and sustainable chemistry.
3. Materials Science
Used in the modification and functionalization of polymers and advanced materials. Bromination via TBATB can impart desired properties such as improved flame retardancy, altered solubility, or provide sites for further chemical modification.
Market Value & Prospects
Current Market Landscape
The demand for high-performance brominating reagents like TBATB is steadily growing, driven by advancements in organic synthesis and increasing needs from the fine chemicals, pharmaceutical, agrochemical, and advanced materials sectors.
Drivers of Market Value
Demand for Efficient Synthesis: The push for more efficient, selective, and atom-economical reactions in R&D and manufacturing solidifies TBATB's role as a key reagent.
Regulatory & Environmental Trends: Stricter environmental regulations favor reagents that enable cleaner processes. TBATB's efficiency and potential for use in controlled reactions support greener chemical production.
R&D and Supply Chain Development: Ongoing research continuously uncovers new applications, while a mature and scaling supply chain helps optimize costs and ensure reliable availability.
Future Outlook
The market for TBATB is poised for positive growth, influenced by key trends:
Greener Production: Adoption of low-waste, energy-efficient manufacturing processes for TBATB itself.
Application Expansion: Exploration of new uses in emerging fields like electronic chemicals, bio-conjugation, and specialized polymer synthesis.
Global Market Integration: With enhancing technical expertise and quality standards, TBATB from leading producers is gaining recognition and competitiveness in the global specialty chemicals market.
Ttetrabutylammonium bromide stands out as an indispensable, high-value reagent in the synthetic chemist's toolkit. Its combination of stability, reactivity, and versatility ensures its continued importance across multiple industries. As the focus on innovative and sustainable chemistry intensifies, TBATB is well-positioned to enable future breakthroughs in chemical synthesis, underpinning its significant and growing market potential.
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