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Tris(pentafluorophenyl)borane

Base Information Edit
  • Chemical Name:Tris(pentafluorophenyl)borane
  • CAS No.:1109-15-5
  • Molecular Formula:C18BF15
  • Molecular Weight:511.985
  • Hs Code.:29039990
  • European Community (EC) Number:414-000-7,601-014-5
  • UNII:I3WU5E2578
  • DSSTox Substance ID:DTXSID6074594
  • Nikkaji Number:J640.919I
  • Wikipedia:Tris(pentafluorophenyl)borane
  • Wikidata:Q3562143
  • Mol file:1109-15-5.mol
Tris(pentafluorophenyl)borane

Synonyms:tris(pentafluorophenyl)borane

Suppliers and Price of Tris(pentafluorophenyl)borane
Supply Marketing:Edit
Business phase:
The product has achieved commercial mass production*data from LookChem market partment
Manufacturers and distributors:
  • Manufacture/Brand
  • Chemicals and raw materials
  • Packaging
  • price
  • TRC
  • Tris(pentafluorophenyl)borane
  • 10mg
  • $ 45.00
  • TRC
  • Tris(pentafluorophenyl)borane
  • 50mg
  • $ 60.00
  • TCI Chemical
  • Tris(pentafluorophenyl)borane >98.0%(NMR)
  • 5g
  • $ 410.00
  • TCI Chemical
  • Tris(pentafluorophenyl)borane >98.0%(NMR)
  • 1g
  • $ 107.00
  • SynQuest Laboratories
  • Tris(pentafluorophenyl)borane 98%
  • 250 mg
  • $ 45.00
  • SynQuest Laboratories
  • Tris(pentafluorophenyl)borane 98%
  • 1 g
  • $ 95.00
  • Strem Chemicals
  • Tris(pentafluorophenyl)borane, min. 97%
  • 1g
  • $ 82.00
  • Strem Chemicals
  • Tris(pentafluorophenyl)borane, min. 97%
  • 5g
  • $ 328.00
  • Strem Chemicals
  • Tris(pentafluorophenyl)borane, min. 97%
  • 25g
  • $ 1186.00
  • Sigma-Aldrich
  • Tris(pentafluorophenyl)borane 95%
  • 100G-A
  • $ 4490.00
Total 124 raw suppliers
Chemical Property of Tris(pentafluorophenyl)borane Edit
Chemical Property:
  • Appearance/Colour:white powder 
  • Vapor Pressure:0.000939mmHg at 25°C 
  • Melting Point:126-131 °C(lit.) 
  • Refractive Index:n20/D 1.41  
  • Boiling Point:327.271 °C at 760 mmHg 
  • Flash Point:151.728 °C 
  • PSA:0.00000 
  • Density:1.707 g/cm3 
  • LogP:4.28930 
  • Storage Temp.:Inert atmosphere,Store in freezer, under -20°C 
  • Sensitive.:Moisture Sensitive 
  • Solubility.:Soluble in hexane, chloroform, dichloromethane, toluene, and pol 
  • Hydrogen Bond Donor Count:0
  • Hydrogen Bond Acceptor Count:15
  • Rotatable Bond Count:3
  • Exact Mass:511.9853526
  • Heavy Atom Count:34
  • Complexity:566
Purity/Quality:

98% *data from raw suppliers

Tris(pentafluorophenyl)borane *data from reagent suppliers

Safty Information:
  • Pictogram(s): HarmfulXn,IrritantXi,ToxicT,DangerousN,Flammable
  • Hazard Codes:Xi,T,N,Xn,F 
  • Statements: 36/37/38-25-67-65-50/53-38-11 
  • Safety Statements: 60-61-62-45-37/39-26-36 
MSDS Files:

SDS file from LookChem

Useful:
  • Canonical SMILES:B(C1=C(C(=C(C(=C1F)F)F)F)F)(C2=C(C(=C(C(=C2F)F)F)F)F)C3=C(C(=C(C(=C3F)F)F)F)F
  • Uses Tris(pentafluorophenyl)borane (CAS# 1109-15-5) is a useful research chemical, used as a catalyst in the metal-free catalytic reductive cleavage of enol ethers via proposed mechanism of tandem hydrosilylation and silicon-?assisted β-?elimination. Tris(pentafluorophenyl)borane also appears as an ancillary ligand in luminescent isocyano Rh(I) complexes. Catalyst in organic transformations; cocatalyst with group IV metallocene alkyls in olefin polymerization. Tris(pentafluorophenyl)borane is used as an excellent activator component in homogeneous Ziegler-Natta chemistry. It is also used as a catalyst for reductions, alkylations, hydrometallation reactions and catalyzed aldol-type reactions. It is a useful Lewis acid and catalyzes hydrosilylation of aldehydes. Further, it is used in olefin polymerization catalysis. It serves as a reagent in the preparation of organometallic complexes. In addition to this, it is useful as polymerization catalysts and used to study the heterolytic cleavage of dihydrogen in associated with tri-tert-butylphosphine.
Technology Process of Tris(pentafluorophenyl)borane

There total 72 articles about Tris(pentafluorophenyl)borane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:
Guidance literature:
bromopentafluorobenzene; With magnesium; In diethyl ether; at 20 ℃;
boron trifluoride diethyl etherate; In toluene; at 0 ℃; for 1h; Schlenk technique; Inert atmosphere;
In diethyl ether; toluene; at 100 ℃; for 1h; Schlenk technique; Inert atmosphere;
DOI:10.1002/anie.202003468
Guidance literature:
bromopentafluorobenzene; With n-butyllithium; In hexane; at -80 ℃; for 0.666667h;
With boron trichloride; In hexane; at -80 - 20 ℃;
DOI:10.1002/anie.200902992
Guidance literature:
bromopentafluorobenzene; With n-butyllithium; In hexane; at -80 ℃; for 1h; Inert atmosphere; Schlenk technique; Glovebox;
boron trichloride; In hexane; at -80 - 20 ℃; for 17h; Inert atmosphere; Schlenk technique; Glovebox;
DOI:10.1039/d0cc02626c
Refernces Edit

Conclusive evidence for an SN2-Si mechanism in the B(C 6F5)3-catalyzed hydrosilylation of carbonyl compounds: Implications for the related hydrogenation

10.1002/anie.200801675

The study provides conclusive evidence for an SN2-Si mechanism in the B(C6F5)3-catalyzed hydrosilylation of carbonyl compounds, which has implications for the related hydrogenation reactions. The researchers used a silane with a stereogenic silicon center as a stereochemical probe to investigate the transition state in the B(C6F5)3-catalyzed hydrosilylation of prochiral acetophenone. They found that the reaction proceeds through a concerted SN2-type displacement at silicon, involving a four-centered cyclic transition state, rather than through a free silylium ion intermediate. This mechanistic understanding is significant for the development of catalytic asymmetric approaches and could guide the design of novel processes in synthetic chemistry. The study also suggests that the efficiency of such reactions may depend on the asymmetric induction of a chiral nonracemic borane catalyst.

Merging Platinum-Catalyzed Alkene Hydrosilylation with SiH4 Surrogates: Salt-Free Preparation of Trihydrosilanes

10.1021/acs.organomet.6b00505

The research describes a novel method for the preparation of trihydrosilanes, which are synthetically useful compounds, by merging platinum-catalyzed alkene hydrosilylation with SiH4 surrogates. The purpose of this study was to develop a safer and more efficient alternative to the hazardous handling of monosilane (SiH4), which is flammable and toxic. The researchers used di(cyclohexa-2,5-dien-1-yl)silane as a stable surrogate for SiH4, which, when combined with various α-olefins in the presence of a platinum catalyst, resulted in the formation of monohydrosilylation adducts. These adducts, with cyclohexa-2,5-dien-1-yl substituents acting as protecting groups, were then treated with catalytic amounts of B(C6F5)3 to liberate Si?H bonds and release benzene, yielding trihydrosilanes in a two-step process without the formation of salt waste. The study successfully demonstrated the scalability of this methodology and provided an alternative route for the preparation of trihydrosilanes, avoiding the need to handle gaseous SiH4, AlkylSiCl3, and AlkylSi(OEt)3, while only releasing benzene as waste.

Direct hydrosilylation by a zirconacycle with β-hydrogen

10.1039/c4dt00658e

The research investigates the unique reactivity of a zirconacycle compound, Cp2Zr{κ2-N(SiHMe2)SiHMeCH2} (1), with a focus on its direct hydrosilylation reaction with formaldehyde. The purpose of the study was to explore the reactions of this compound with a series of nucleophilic and electrophilic agents, as well as its behavior with carbonyls, to develop a rationale for the unexpected hydrosilylation activity. The conclusions drawn from the research indicate that the compound 1, despite containing classical 2-center-2-electron SiH groups, reacts with formaldehyde at the exocyclic SiH to form a methoxysilyl group, a transformation that diverges from the reactions of β-H free analogs. This reactivity is attributed to the metallacyclic structure of 1, which may enhance the reactivity of the exocyclic β-hydrogen or limit non-classical interactions that would otherwise stabilize the reactive β-hydrogen. Key chemicals used in the process include formaldehyde, carbon monoxide, tris(perfluorophenyl)borane (B(C6F5)3), and various donor ligands such as OPEt3, PMe3, pyridine, and DMAP.

Tris(pentafluorophenyl)borane-catalyzed three-component reaction for the synthesis of 1,8-dioxodecahydroacridines under solvent-free conditions

10.1055/s-2008-1067039

The study presents a mild and efficient method for synthesizing 1,8-dioxodecahydroacridines via a three-component reaction involving a 1,3-dione, an aldehyde, and an amine, catalyzed by tris(pentafluorophenyl)borane [B(C6F5)3] under solvent-free conditions. The chemicals involved include 1,3-cyclohexanedione as the 1,3-dione, various aldehydes (such as benzaldehyde, aliphatic aldehydes, and heteroaromatic aldehydes), and different amines (like aniline and 4-fluoroaniline). The role of B(C6F5)3 is to act as a Lewis acid catalyst, facilitating the reaction to proceed at room temperature with high yields of the desired 1,8-dioxodecahydroacridines. The study highlights the advantages of this method over traditional Hantzsch reactions, such as shorter reaction times, milder conditions, and higher yields, making it a significant advancement in the synthesis of this class of compounds, which have applications in pharmaceuticals, dyes, and materials science.

Isolobal zwitterionic niobium and tantalum imido and zirconium monocyclopentadienyl complexes: Theoretical and methyl methacrylate polymerization studies

10.1021/om701068h

The study investigates the synthesis and characterization of zwitterionic niobium and tantalum imido complexes, specifically focusing on their potential as catalysts for methyl methacrylate (MMA) polymerization. The researchers synthesized various complexes using trichloro derivatives [MCl3(NR)(py)2] (where M = Nb or Ta, R = tBu or aryl) and reacted them with lithium aryloxides (LiOAr) to obtain imido aryloxo complexes. They also employed benzyl magnesium chloride ([BzMgCl]) for alkylation, resulting in tribenzyl derivatives. Lewis acids such as B(C6F5)3 and Al(C6F5)3 were used to generate zwitterionic complexes from the tribenzyl derivatives, facilitating the exploration of their catalytic activity in MMA polymerization. The study highlights the role of these chemicals in modifying the reactivity and stability of high-valent metal complexes for potential applications in polymerization processes.

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