15522-59-5

Basic information

• Product Name: TETRA-N-BUTYLAMMONIUM TETRAPHENYLBORATE
• Synonyms: TETRA-N-BUTYLAMMONIUM TETRAPHENYLBORATE;TETRAPHENYLBORON TETRABUTYLAMMONIUM;TETRABUTYLAMMONIUM TETRAPHENYLBORATE;ammonium,tetrabutyl-,tetraphenylborate(1-);borate(1-),tetraphenyl-,N,N,N-tributyl-1-butanaminium;tetrabutylammoniumtetraphenylborate(1-);TETRABUTYLAMMONIUM TETRAPHENYLBORATE, EL ECTROCHEM. GRADE;TETRABUTYLAMMONIUM TETRAPHENYLBORATE, 99 %
• CAS NO: 15522-59-5
• Molecular Formula: C₁₆H₃₆N*C₂₄H₂₀B
• Molecular Weight: 561.69
• EINECS: 239-562-9
• Product Categories: Ammonium Polyhalides, etc. (Quaternary);B (Classes of Boron Compounds);Quaternary Ammonium Compounds;Tetraphenylborates
• Mol File: 15522-59-5.mol

Chemical Properties

• Melting Point: 230-236 °C(lit.)
• Appearance: white crystals or powder
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: acetonitrile: 0.1 g/mL, clear, colorless
• Water Solubility: Soluble in pyridine, acetone, water.
• Sensitive: Hygroscopic
• Stability: Stable. Incompatible with strong oxidizing agents. Hygroscopic.
• BRN: 3857215
• CAS DataBase Reference: TETRA-N-BUTYLAMMONIUM TETRAPHENYLBORATE(CAS DataBase Reference)
• NIST Chemistry Reference: TETRA-N-BUTYLAMMONIUM TETRAPHENYLBORATE(15522-59-5)
• EPA Substance Registry System: TETRA-N-BUTYLAMMONIUM TETRAPHENYLBORATE(15522-59-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 8-9
• Hazardous Substances Data: 15522-59-5(Hazardous Substances Data)

Usage

Uses

Used in Electrotunable Materials:
TETRA-N-BUTYLAMMONIUM TETRAPHENYLBORATE is used as a key component in the preparation of electrotunable materials for their ability to alter the properties of materials in response to an electric field. This application is particularly relevant in the development of advanced materials with tunable optical, electronic, and catalytic properties.
Used in Nanoplasmonic Liquid Mirrors:
In the field of nanoplasmonics, TETRA-N-BUTYLAMMONIUM TETRAPHENYLBORATE is used as a crucial ingredient in the creation of electrotunable nanoplasmonic liquid mirrors. These mirrors exhibit unique optical properties that can be manipulated through the application of an electric field, making them valuable in various optical and photonic applications.
Used in Sensor Applications:
TETRA-N-BUTYLAMMONIUM TETRAPHENYLBORATE also finds use in the development of sensor applications due to its electrotunable nature. The compound's ability to respond to electric fields can be harnessed to create sensors with enhanced sensitivity and selectivity, which can be beneficial in various analytical and diagnostic applications.

InChI:InChI=1/C24H20B.C16H36N/c1-5-13-21(14-6-1)25(22-15-7-2-8-16-22,23-17-9-3-10-18-23)24-19-11-4-12-20-24;1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4/h1-20H;5-16H2,1-4H3/q-1;+1

Upstream product

• 1643-19-2 tetrabutylammomium bromide 
• 143-66-8 sodium tetraphenyl borate 
• 1643-19-2 tetra-n-butylammonium bromide 

Downstream Products

• 882-33-7 diphenyldisulfane 
• 122905-48-0 {MoI(CO)3(η6-C6H5Me)}BPh4 
• 113747-48-1 (η2,η3:σ',η'4-C16H16)(η5-cyclopentadienyl)2dirhodium bis(tetraphenylborate) 
• 190205-04-0 [(1,4,7-trimethyl-1,4,7-triazacyclononane)2Zn2(μ-Br)3]BPh4 
• 190205-02-8 [(1,4,7-trimethyl-1,4,7-triazacyclononane)2Zn2(μ-Cl)3]BPh4 
• 1200628-21-2 W₂(2,2,-dipyridylamido)₄ 

Relevant articles and documents

Preparation method of tetraphenylborate

The invention discloses a preparation method of tetraphenylborate. Sodium tetraphenylborate reacts with a quaternary salt compound under the synergistic effect of water and an organic solvent to prepare a tetraphenylborate product, and the organic solvent is an organic solution which can dissolve the quaternary salt compound and does not participate in the reaction. According to the method, the process of almost quantitatively reacting sodium tetraphenylborate with the quaternary salt compound in a mixed reaction system consisting of water and an organic solution to obtain an organic quaternary tetraphenylborate product is realized, the product purity is high, and the byproduct sodium salt is completely dissolved in water, so that interference byproducts are avoided, the method is suitable for efficient and high-purity large-scale preparation and production of organic tetraphenylborate.

Two distinct allosteric active sites regulate guest binding within a Fe8Mo1216+ cubic receptor

The binding of phosphine ligands to molybdenum sites on the faces of a supramolecular cube served to inhibit allosterically the encapsulation of a neutral or anionic guest. The edges of the cube also provided a distinct second allosteric site, where the binding of tetraphenylborate also allosterically inhibited anion binding in the cubes cavity. The two allosteric sites were shown to regulate the binding of an anionic guest either independently or in concert. The use of a tertiary amine as an allosteric effector also enabled a phosphine guest to be ejected from the cubes cavity into solution, to generate phosphine complexes with other metal ions.

Synthesis of nanometer-sized, rigid, and hydrophobic anions

Size matters: The strategy of divergent dendronization allows for the synthesis of unprecedented large, rigid, and bulky anions (see picture). Their size, density, and chemical nature of surface can be tailored to obtain more hydrophobic, less nucleophilic, and more weakly coordinating anions. Copyright

The electrooxidation of the tetraphenylborate ion revisited

The electrochemistry of the tetraphenylborate ion, BPh4-, has been studied by cyclic voltammetry and coulometry in water, methanol, ethanol, acetonitrile, acetone, dimethylformamide and dichloromethane under an N2 atmosphere. While a one-electron and somewhat irreversible oxidation (with an E1/2 of 0.87 V vs. SCE at a glassy carbon electrode) is observed in dichloromethane, eqn. (i), BPh4- ? ·BPh4 + e- the oxidation is somewhat complicated in all other solvents by the occurrence of several consecutive reactions. Epa, the anodic peak potential in cyclic voltammetry, changes from 0.41 V vs. SCE in water to 0.94 V vs. SCE in dimethylformamide at a glassy carbon electrode. The variation in Epa with solvent (S) is explained by invoking reaction (ii). ·BPh4 + S → S-BPh3 + ·Ph. The coulometric results in solvents other than dichloromethane indicate a disproportionation of S-BPh3, eqn. (iii). 2S-BPh3 → S-BPh2+ + BPh4- + S.

Synthesis and structural characterization of boron subphthalocyaninates

Halosubphthalocyaninatoboron, [B(X)spc] (X = F, Cl, Br) is obtained by heating phthalonitrile with boron trihalide in quinoline (X = F) or the corresponding halobenzene, resp. [B(C6H5)spc] is prepared from phthalonitrile and tetraphenylborate or tetraphenyloboron oxide, resp. [B(OR)spc] (R = H, CH(CH3)2, C(CH3)3, C6H5) is synthesized by bromide substitution of [B(Br)spc] in pyridine/ HOR. Substitution of [B(Br)spc] in carboxylic acids yields [B(OOCR)spc] (R = H, CX3 (X = H, Cl, F), CH2X (X = Cl, C6H5), C6H5). All subphthalocyaninates are characterized electrochemically and by UV-VIS, IR/FIR, resonance Raman, and 1H/10B-NMR spectroscopy. Typical B-X stretching vibrations are at 622 (X = Br), 950 (Cl), 1063 (F), 1096 cm-1 (OH) as well as between 1119 and 1052 cm-1 (OR) resp. 985 and 1028cm-1 (OOCR). The difference v(C=O)-v(C-O) > 400 cm-1 confirms the unidentate coordination of the carboxylato ligands. According to the crystal structure analysis of [B(OH)s,pc], [B(OH)spc] · 2H2O, [B(C6H5)spc], [B(OC(CH3)3)spc], [B(OOCCH3)spc] · 0.5H2O · C2H5OH and [B(OOCCH3)spc] · 0.4H2O · 1.1 C5H5N the spc ligand is concavely distorted. This saucer shaped conformation is independent of the acido ligands and the presence of solvate. The outermost C atomes are vertically displaced in part by more than 2 A from the N, plane. The B atom is in a distorted tetrahedral coordination geometry. It is displaced by ca 0.64 A out of the NI plane towards the acido ligand. The average B-N distance is 1.500 A, and the B-O distances range from 1.418(5) to 1.473(2) A.

One-electron oxidation of (η4-cot)RhCp: Rearrangements of the radical cation and of the resulting dimerization product

The complex (η4-Cot)RhCp (Cot = cyclooctatetraene; 3) undergoes an irreversible one-electron oxidation to a transient radical cation. Detailed voltammetric studies suggest that the radical rearranges to (η5-C8H8)RhCp+ before dimerizing through the allyl radical section of the C8 ring. Anodic or chemical oxidation (using [FeCp2]+ or AgPF6) in CH2Cl2 gives the C-C bonded dimer [(η5:η′5-C16H 16)Rh2Cp2][PF6]2 (4) which thermally isomerizes to [(η2,η3:η′2,η′ 3-C16H16)Rh2Cp2][PF 6]2 (2b) and then to [η2,η3:σ′,η′ 4-C16H16)Rh2Cp2][PF 6]2 (5). The asymmetric species 5 has been fully characterized as the [BPh4]- salt by single-crystal X-ray diffraction. Crystallographic data: C74H66B2Rh2, a = 20.421 (5) A?, b = 15.198 (2) A?, c = 19.528 (4) A?, β = 114.10 (2)°, space group P21/c, R = 0.083, Rw = 0.077. The dication of 5 contains two rhodium atoms, each carrying an η5-cyclopentadienyl ring bridged [Rh?Rh = 6.514 (2) A?] by a C16H16 ligand. The ligand is formally derived from two Cot molecules by formation of three C-C bonds linking the two original C8 rings. The resultant tetracyclic ligand bonds via σ,η4- and η2,η3-linkages to the two rhodium atoms, acting as a five-electron donor to each.