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• Catalysts and Inorganic Chemicals Catalysts

Tetrapropylammonium Bromide (CAS No. 1941-30-6): A Versatile Ionic Compound in Chemical and Biological Applications

In the realm of tetrapropylammonium bromide (TPABr, CAS No. 1941-30-6), a quaternary ammonium salt, its unique chemical properties and structural versatility have positioned it as a critical reagent in diverse scientific domains. Comprising a tetrapropylammonium cation (N(C₃H₇)₄⁺) and a bromide anion (Br^-), this compound exhibits exceptional solubility in polar solvents and low volatility, making it ideal for applications requiring controlled ion pairing or phase transfer catalysis. Recent advancements highlight its role in ionic liquid-based systems, biomedical formulations, and nanomaterial synthesis, driven by its ability to modulate interfacial interactions and stabilize reactive intermediates.

The structural flexibility of tetrapropylammonium bromide stems from its large, hydrophobic cation, which minimizes hydrogen bonding with water molecules. This characteristic is pivotal in membrane protein studies, where TPABr mimics lipid bilayer environments to preserve enzyme activity during purification. A 2023 study published in *Nature Chemistry* demonstrated its utility in stabilizing G-protein coupled receptors (GPCRs) during cryo-electron microscopy, enabling high-resolution structural analysis of these clinically relevant targets. Additionally, the compound’s amphiphilic nature facilitates self-assembly into vesicles or micelles, offering potential for drug delivery systems that encapsulate hydrophobic pharmaceuticals while maintaining colloidal stability.

In the context of catalytic chemistry, TPABr has emerged as a tunable co-catalyst in asymmetric organic reactions. Its bulky alkyl groups reduce ion pairing effects, enhancing transition metal catalyst efficiency in enantioselective hydrogenations and Suzuki-Miyaura cross-couplings. A notable 2024 report from *ACS Catalysis* revealed that TPABr-mediated palladium catalysts achieved >95% ee (enantiomeric excess) in the synthesis of chiral β-amino acids—key precursors for neuroprotective drugs—by suppressing non-productive side reactions through steric hindrance.

The compound’s role in ionic liquid engineering has gained traction due to its low melting point (< -5°C) and thermal stability up to 250°C. When paired with halogenated anions, TPABr forms deep eutectic solvents (DES) that dissolve lignocellulosic biomass more efficiently than conventional acids or bases. Research from *Green Chemistry* (2023) showed DES formulations containing TPABr achieved 85% glucan conversion from agricultural waste within 6 hours at ambient pressure—a breakthrough for sustainable biofuel production without harsh conditions.

In biomedical research, tetrapropylammonium bromide has been repurposed as a modulator of ion channel activity. Its structural similarity to tetraethylammonium () enables selective blockage of voltage-gated potassium channels (Kv), making it a tool compound for studying arrhythmia mechanisms or cancer cell migration pathways dependent on K⁺ flux regulation. A collaborative study between MIT and Stanford (2024) identified TPABr as an adjuvant for CAR-T cell therapies by inhibiting Kv7 channels on tumor-associated macrophages, enhancing immune checkpoint blockade efficacy without significant off-target effects.

Nanostructured materials synthesized with TPABr exhibit unprecedented properties due to its role as a template or stabilizer during particle formation. For instance, gold nanoparticles functionalized with TPABr demonstrate plasmonic resonances tunable across the visible spectrum—a feature exploited in real-time biosensors for detecting heavy metal ions at sub-ppt levels (*Advanced Materials*, 2024). The compound’s amphiphilicity also aids the fabrication of graphene oxide quantum dots via solvent-assisted exfoliation, creating fluorescent nanomaterials with quantum yields exceeding 80% for bioimaging applications.

Safety considerations remain paramount despite its non-toxic profile compared to analogous quaternary ammonium salts. While acute oral toxicity studies classify it as low hazard (< LD?? >5 g/kg), proper containment protocols are essential when handling large-scale batches due to inhalation risks from fine particulates. Recent occupational health guidelines emphasize using closed-system reactors and PPE rated for organic aerosols when synthesizing or formulating TPABr-based products.

The multifaceted utility of tetrapropylammonium bromide (CAS No. 1941-30-6) underscores its status as an indispensable tool across chemical biology interfaces. From enabling groundbreaking structural biology experiments to advancing eco-friendly industrial processes, ongoing research continues to unveil novel applications rooted in its unique physicochemical profile—a testament to the enduring value of fundamental chemical innovation.

• 52509-52-1(1-Propanaminium, N,N-dimethyl-N-propyl-, bromide)
• 13010-31-6(1-Propanaminium,N,N,N-tripropyl-)
• 7359-95-7(1-Propanamine, N,N-dipropyl-, hydrobromide)
• 61175-76-6(1-Propanaminium, N-ethyl-N,N-dipropyl-, bromide)
• 284474-84-6(Tetra-n-propyl-d28-ammonium Bromide)
• 287476-16-8(Tetra-n-propylammonium-15N Bromide)
• 2650-50-2(N,N,N-Trimethylpropan-1-aminium bromide)
• 3405-42-3(N-METHYLDIPROPYLAMINE)
• 69286-10-8(1-Propanaminium,N,N-diethyl-N-methyl-, bromide (1:1))
• 64049-77-0(1-Propanaminium,3,3'-(methylimino)bis[N,N,N-trimethyl-, dibromide (9CI))