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Merck
CN

442593

Sigma-Aldrich

Tris(pentafluorophenyl)borane

greener alternative

95%

Synonym(s):

Perfluorotriphenylboron

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About This Item

Linear Formula:
(C6F5)3B
CAS Number:
Molecular Weight:
511.98
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.23
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Quality Level

Assay

95%

form

powder

greener alternative product characteristics

Catalysis
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mp

126-131 °C (lit.)

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SMILES string

Fc1c(F)c(F)c(B(c2c(F)c(F)c(F)c(F)c2F)c3c(F)c(F)c(F)c(F)c3F)c(F)c1F

InChI

1S/C18BF15/c20-4-1(5(21)11(27)16(32)10(4)26)19(2-6(22)12(28)17(33)13(29)7(2)23)3-8(24)14(30)18(34)15(31)9(3)25

InChI key

OBAJXDYVZBHCGT-UHFFFAOYSA-N

General description

Tris(pentafluorophenyl)borane is a highly fluorinated, boron-based Lewis acid significantly stronger than its inorganic counterpart, BF₃. Unlike the pentafluorides of heavier group 15 elements, B(C₆F₅)₃ exhibits no oxidizing properties. Its pronounced electrophilicity and thermal stability make it a versatile reagent, capable of forming stable adducts with neutral and weak Lewis bases, as well as accepting anionic ligands from metal complexes. These attributes render B(C₆F₅)₃ highly valuable in organometallic catalysis, doping of organic semiconductors, and both solution-phase and vapor-phase material fabrication, including thin-film deposition.
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Application

Tris(pentafluorophenyl)borane can be used as:

  • A surface passivation material to enhance the performance and stability of perovskite solar cells.
  • A p-type dopant and a Lewis acid receptor in poly(3-hexylthiophene) (P3HT)-based organic field-effect transistors (OFETs) for environmental ammonia monitoring.
  • A Lewis acid catalyst in the synthesis of advanced siloxane materials via Piers–Rubinsztajn reaction.
  • A catalyst in the cyclopropanation of styrenes with aryldiazoacetates to synthesize cyclopropane derivatives under mild conditions.
  • A versatile reagent widely used in the preparation of d0 arene and other organometallic complexes, useful as polymerization catalysts.
  • Used with tri-tert-butylphosphine (570958) to study the heterolytic cleavage of dihydrogen at room temperature and one atmosphere pressure.

Features and Benefits

A versatile reagent widely used in the preparation of d0 arene and other organometallic complexes useful as polymerization catalysts.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Facile heterolytic cleavage of dihydrogen by phosphines and boranes.
Gregory C Welch et al.
Journal of the American Chemical Society, 129(7), 1880-1881 (2007-01-31)
Tris (pentafluorophenyl) borane-catalyzed cyclopropanation of styrenes with aryldiazoacetates
Mancinelli, Joseph P and Wilkerson-Hill, Sidney M
ACS Catalysis, 10, 11171-11176 (2020)
Organometallics, 15, 3600-3600 (1996)
Hans Fuhrmann et al.
Inorganic chemistry, 35(23), 6742-6745 (1996-11-06)
The reaction of trimethylsilyl-substituted 2-aminopyridines with mixed chloro(dialkylamido)metal complexes (titanium and zirconium) leads via amine elimination to octahedral group 4 metal complexes that contain amine, amido, and aminopyridinato ligands. The X-ray crystal structure analyses of (4-Me-TMS-APy)(NMe(2))(HNMe(2))TiCl(2) (1) (crystallographic data: P2(1)/c
Dan Voicu et al.
ChemSusChem, 8(24), 4202-4208 (2015-11-27)
Separation of gaseous olefins and paraffins is one of the most important separation processes in the industry. Development of new cost-effective technologies aims at reducing the high energy consumption during the separation process. Here, we took advantage of the reaction

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