Tris(pentafluorophenyl)borane

Base Information

• 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

Synonyms:tris(pentafluorophenyl)borane

Chemical Property of Tris(pentafluorophenyl)borane

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:

99.9% ^*data from raw suppliers

Tris(pentafluorophenyl)borane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi,T,N,F
• 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:

Reference yield: 95.0%

bromopentafluorobenzene (344-04-7) + boron trifluoride diethyl etherate (109-63-7) → tris(pentafluorophenyl)borate (1109-15-5)

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

Reference yield: 85.0%

bromopentafluorobenzene (344-04-7) → tris(pentafluorophenyl)borate (1109-15-5)

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

Reference yield: 84.0%

bromopentafluorobenzene (344-04-7) + boron trichloride (10294-34-5) → tris(pentafluorophenyl)borate (1109-15-5)

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

upstream raw materials:

pentafluorophenyl lithium

tris(perfluorophenyl)borane-acetonitrile adduct

bromopentafluorobenzene

2,3,4,5,6-pentafluorophenylmagnesium bromide

Downstream raw materials:

1,2,3,4,5-pentafluoro-6-iodobenzene

perfluorotoluene

Li[MeB(C₆F₅)3]

triphenylmethyl [(tris(pentafluorophenyl)boran)2 cyanide]

Refernces

• 1、 B?hr, Alexander,Wilkins, Lewis C.,Ollegott, Kevin,Kariuki, Benson M.,Melen, Rebecca L.. "σ- versus π-activation of alkynyl benzoates using B(C6F5)3". . p. 4530 - 4547. Retrieved 2015.
• 2、 Massey,Park. "". . p. 245,247. Retrieved 1964.
• 3、 Bl?sing, Kevin,Bresien, Jonas,Labbow, René,Michalik, Dirk,Schulz, Axel,Thomas, Max,Villinger, Alexander. "Borane Adducts of Hydrazoic Acid and Organic Azides: Intermediates for the Formation of Aminoboranes". . p. 6540 - 6544. Retrieved 2019.
• 4、 Aramaki, Yoshitaka,Hotta, Mao,Imaizumi, Naoki,Kumagai, Jun,Ooi, Takashi. "Exploiting single-electron transfer in Lewis pairs for catalytic bond-forming reactions". . p. 4305 - 4311. Retrieved 2020.
• 5、 Stockland Jr., Robert A.,Jordan, Richard F.. "Reaction of vinyl chloride with a prototypical metallocene catalyst: Stoichiometric insertion and β-Cl elimination reactions with rac-(EBI)ZrMe+ and catalytic dechlorination/oligomerization to oligopropylene by rac- (EBI)ZrmE2/MAO [15]". . p. 6315 - 6316. Retrieved 2000.
• 6、 Gazis, Theodore A.,Mohajeri Thaker, Bayan A. J.,Willcox, Darren,Ould, Darren M. C.,Wenz, Jan,Rawson, Jeremy M.,Hill, Michael S.,Wirth, Thomas,Melen, Rebecca L.. "1,3-Carboboration of iodonium ylides". . p. 3345 - 3348. Retrieved 2020.
• 7、 Mori, Toshiaki,Yoshigoe, Yusuke,Kuninobu, Yoichiro. "Control of Multicolor and White Emission by Adjusting the Equilibrium between Fluorophores, Lewis Acids, and Their Complexes in Polymers". . p. 14457 - 14461. Retrieved 2019.
• 8、 Ren, Kangtai,Malpert, John H,Gu, Haiyan,Li, Huiying,Neckers, Douglas C. "Synthesis, properties and photolysis of new iodonium tetrakis(pentafluorophenyl)gallate photoinitiators and comparison with their indate and aluminate analogs". . p. 5267 - 5273. Retrieved 2002.
• 9、 Helmecke, Lucas,Spittler, Michael,Schmidt, Bernd M.,Czekelius, Constantin. "Metal-Free Iodoperfluoroalkylation: Photocatalysis versus Frustrated Lewis Pair Catalysis". supporting information. p. 123 - 134. Retrieved 2020/09/02.
• 10、 Mayer, Robert J.,Hampel, Nathalie,Ofial, Armin R.. "Lewis Acidic Boranes, Lewis Bases, and Equilibrium Constants: A Reliable Scaffold for a Quantitative Lewis Acidity/Basicity Scale". supporting information. p. 4070 - 4080. Retrieved 2021/01/29.