341-02-6

Basic information

• Product Name: TRIPHENYLCARBENIUM TETRAFLUOROBORATE
• Synonyms: triphenyl-methyliutetrafluoroborate(1-);TRITYLIUM TETRAFLUOROBORATE;TRITYL FLUOROBORATE;TRIPHENYLCARBENIUM TETRAFLUOROBORATE;TRIPHENYLMETHYL TETRAFLUOROBORATE;trityl tetrafluoroborate;Triphenylcarbeniumtetrafluoroborate,98%;Methylium, triphenyl-, tetrafluoroborate(1-)
• CAS NO: 341-02-6
• Molecular Formula: BF₄*C₁₉H₁₅
• Molecular Weight: 330.13
• EINECS: 206-433-3
• Product Categories: B (Classes of Boron Compounds);Tetrafluoroborates
• Mol File: 341-02-6.mol

Chemical Properties

• Melting Point: 205-215 °C (dec.)(lit.)
• Appearance: Ochre-yellow to brown to dark green/Crystalline Powder, Crystals and/or Chunks
• Storage Temp.: 2-8°C
• Water Solubility: Insoluble in water. Soluble in methanol.
• Sensitive: Moisture Sensitive
• Stability: Hygroscopic, Light-sensitive
• BRN: 5085649
• CAS DataBase Reference: TRIPHENYLCARBENIUM TETRAFLUOROBORATE(CAS DataBase Reference)
• NIST Chemistry Reference: TRIPHENYLCARBENIUM TETRAFLUOROBORATE(341-02-6)
• EPA Substance Registry System: TRIPHENYLCARBENIUM TETRAFLUOROBORATE(341-02-6)

Safety Data

• Hazard Codes: C,Xi
• Statements: 14-34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• F: 8-10-21
• TSCA: T
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 341-02-6(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
TRIPHENYLCARBENIUM TETRAFLUOROBORATE is used as a reagent for the direct synthesis of 1,1-diphenyl-3-arylindanes, which are important intermediates in the production of various pharmaceuticals and chemical compounds.
Used in the Synthesis of Substituted Dihydroazulene Photoswitches:
In the field of photochemistry, TRIPHENYLCARBENIUM TETRAFLUOROBORATE is used as a reactant in the synthesis of substituted dihydroazulene photoswitches. These photoswitches are crucial in the development of light-responsive materials and systems, such as optical data storage and molecular switches.
Used in Carbene-based Lewis Pairs for Hydrogen Activation:
TRIPHENYLCARBENIUM TETRAFLUOROBORATE is employed as a reactant in the formation of carbene-based Lewis pairs, which are essential for hydrogen activation. This process is vital in the development of more efficient and environmentally friendly chemical reactions.
Used in 1,3-Dipolar Cycloaddition Reactions for the Preparation of α-Amino-β-Hydroxy Esters:
In the pharmaceutical industry, TRIPHENYLCARBENIUM TETRAFLUOROBORATE is used as a reactant in 1,3-dipolar cycloaddition reactions, leading to the preparation of α-amino-β-hydroxy esters. These compounds are key building blocks in the synthesis of various biologically active molecules and pharmaceuticals.
Used in the Oxidation of Allenic Compounds:
TRIPHENYLCARBENIUM TETRAFLUOROBORATE is utilized as a reactant in the oxidation of allenic compounds, which are important precursors in the synthesis of various organic molecules, including pharmaceuticals, agrochemicals, and natural products.
Used in Mukaiyama Aldol Addition Reactions:
In organic chemistry, TRIPHENYLCARBENIUM TETRAFLUOROBORATE is used as a reactant in Mukaiyama aldol addition reactions, which are crucial for the synthesis of complex organic molecules, such as natural products and pharmaceuticals.
Used in Ionic Hydrogenation as a Counteranion and Ligand Source:
TRIPHENYLCARBENIUM TETRAFLUOROBORATE is employed in ionic hydrogenation reactions, where it serves as a counteranion and ligand source. This application is significant in the development of more efficient and selective hydrogenation processes, which are essential in the production of various chemicals and pharmaceuticals.

InChI:InChI=1/C19H15.BF4/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18;2-1(3,4)5/h1-15H;/q+1;-1

Upstream product

• 427-36-1 trityl fluoride 
• 75-01-4 chloroethylene 
• 76-83-5 trityl chloride 
• 557-99-3 acetyl fluoride 
• 519-73-3 triphenylmethane 
• 76-84-6 triphenylmethyl alcohol 
• 71-43-2 benzene 
• 7637-07-2 boron trifluoride 
• 2261-02-1 acetylium tetrafluoroborate 
• 14104-20-2 silver tetrafluoroborate 

Downstream Products

• 51208-34-5 1,1-dimethoxy-2,6-diphenyl-4-trityl-1λ⁵-phosphinine 
• 55686-04-9 2-Phenyl-4-(triphenylmethyl)-2-oxazolin-5-on 
• 51905-36-3 C₂₉H₃₀ 
• 968-39-8 Triphenylmethylethylether 
• 67370-43-8 3-benzo[1,3]dithiol-2-yl-2,5-dimethyl-4-trityl-pyrrole 
• 353-66-2 dimethyldifluorosilane 
• 519-73-3 triphenylmethane 
• 210362-80-4 allyldimethylfluorosilane 
• 72997-00-3 But-3-enyl-fluoro-dimethyl-silane 
• 97684-09-8 1,1,1,7,7,7-Hexaphenyl-2,6-dithiaheptan 
• 55549-96-7 4-Pentenyl-dimethylfluorsilan 

Relevant articles and documents

Carbene-based lewis pairs for hydrogen activation

A series of Lewis acidbase pairs containing sterically demanding carbenes were investigated for hydrogen activation that could potentially be reversible for use in hydrogen storage applications. When electron-rich boranes are employed as electrophiles, the imidazolium cation is reduced to a 2H-imidazoline (aminal). The aminals were synthesized independently by reduction of imidazolium cations with strong reducing agents. Carbocations were also found to act as electrophiles for hydrogen activation. Preliminary results revealed that it is possible to reduce an alcohol to an alkane using hydrogen gas as a reducing agent in these systems. Finally, it was demonstrated that a transition metal can be used as an electrophile to activate hydrogen through heterolytic cleavage.

Synthesis and structure of tritylium salts

Several tritylium compounds [Ph3C][A] have been isolated by salt metathesis or halide abstraction reactions starting from Ph3C-X (X = halogen) and Lewis acids in good yields (A = BF4, BCl4, AlCl4, GaCl4, PF6, AsF6, SbF6, SbCl6, CHB11H5Cl6, CHB11Cl11, CHB11H5Br6, CF3COO, CF3SO3, N3). The structures of 15 tritylium salts bearing different types of weakly coordinating anions (A-) have been determined. The structures are discussed on the basis of ion pairing versus covalent bond formation and solid-state interactions in comparison with gas-phase data.

Optimized synthesis and detailed NMR spectroscopic characterization of the 1,8a-dihydroazulene-1,1-dicarbonitrile photoswitch

An economical and effective protocol for large scale synthesis of the 2-phenyl-1,8adihydroazulene-1,1-dicarbonitrile (DHA) photoswitch has been developed. This compound is ring-opened by light to a vinylheptafulvene (VHF), which is thermally closed back to DHA. This compound serves as an important starting material for dihydroazulene photoswitches incorporating a substituent in the seven-membered ring and as a reference compound for comparison of properties. A detailed NMR spectroscopic characterization has allowed the assignment of all proton and carbon signals. In addition, the compound was characterized by Xray crystallography. A correlation between the rate constant for thermal ring-closure of VHF to DHA and empirical parameters of solvent polarity (ET (30)) was established. ARKAT-USA, Inc.

Synthesis and Isolation of Polytrityl Cations by Utilizing Hexaphenylbenzene and Tetraphenylmethane Scaffolds

The successful isolation of stable (and soluble) hexa- and tetratrityl cations based on hexaphenyl-benzene and tetraphenylmethane scaffold has been accomplished by using readily available starting materials. These robust polytrityl cations can be isolated in crystalline form and stored indefinitely at 0 °C. Their structures have been established by 1H/ 13C NMR spectroscopy and by UV-vis spectroscopy. The structures of these polytrityl cations were further confirmed by quantitative transformations to the reduced (poly)triphenylmethyl derivatives by hydride transfer from triethylsilane, cycloheptatriene, or a borane-dimethyl sulfide complex.

Cyclisation reactions of 2-substituted biphenyl-2'-yldiazonium salts leading to O-alkyldibenzofuranium and S-alkyldibenzothiophenium salts: Modified Meerwein reagents

The preparation of 2-amino-2'-methoxybiphenyl and 2-amino-2'-thiomethoxybiphenyl and analogues and their transformation into diazonium salts and hence into dibenzofuranium and dibenzothiophenium salts is described together with their use as alkylating agents.