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CAS RN: 1109-15-5 | Product Number: T2313

Tris(pentafluorophenyl)borane


Purity: >98.0%(NMR)
Synonyms:
Documents:
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Product Number T2313
Purity / Analysis Method >98.0%(NMR)
Molecular Formula / Molecular Weight C__1__8BF__1__5 = 511.98  
Physical State (20 deg.C) Solid
Storage Temperature <0°C
Store Under Inert Gas Store under inert gas
Condition to Avoid Hygroscopic,Heat Sensitive
CAS RN 1109-15-5
Reaxys Registry Number 2931347
PubChem Substance ID 87558752
Merck Index (14) 9755
MDL Number

MFCD00269813

Specifications
Appearance White to Gray to Brown powder to crystal
Purity(NMR) min. 98.0 atom%
Water max. 1.0 %
Properties (reference)
Melting Point 128 °C
Maximum Absorption Wavelength 306(Toluene) nm
Solubility (soluble in) Toluene
GHS
Pictogram Pictogram
Signal Word Warning
Hazard Statements H315 : Causes skin irritation.
H319 : Causes serious eye irritation.
Precautionary Statements P264 : Wash skin thoroughly after handling.
P280 : Wear protective gloves/ eye protection/ face protection.
P302 + P352 : IF ON SKIN: Wash with plenty of water.
P337 + P313 : If eye irritation persists: Get medical advice/ attention.
P362 + P364 : Take off contaminated clothing and wash it before reuse.
P332 + P313 : If skin irritation occurs: Get medical advice/ attention.
Related Laws:
Transport Information:
HS Number 2931900090
Application
Deuteration of Aromatic and Heteroamomatic Compounds Catalyzed by Tris(pentafluorophenyl)borane

T2313

Experimental procedure: N,N-Dibenzylaniline (140 mg, 0.513 mmol), tris(pentafluorophenyl)borane (17.0 mg, 0.033 mmol), D2O (306 mg, 15.3 mmol) are placed in a sealed tube. The reaction mixture is stirred at 80 °C for 24 h. After the reaction is completed, the reaction mixture is purified by silica gel column chromatography (cyclohexane:ethylacetate = 20:1) to afford N,N-dibenzylaniline-2,4,6-d3 (134 mg) in 95% yield.

References


Application
High Throughput Sequence-controlled Oligosiloxane Synthesis

References


Application
Frustrated Lewis Pair (FLP)-induced Hydrogenations of Silyl Enol Ethers

References


Application
Tri(cyclohexa-2,5-dien-1-yl)silane: A Stable and Easy-to-handle Surrogate of Monosilane (SiH4)

Synthesis of multisubstituted silanes:
In a glove box, a Schlenk tube is charged with an alkene (0.300 mmol). In two vials are weighed B(C6F5)3 (7.7 mg, 15 µmol) and tri(cyclohexa-2,5-dien-1-yl)silane (1, 28.0 mg, 0.105 mmol). All the sealed containers are taken out of the glove box, and the Schlenk tube is connected to a N2 line. Under a N2 counterflow are subsequently added 0.3 mL of CH2Cl2, 1 then B(C6F5)3. The tube is completely sealed and stirred at room temperature for 24 h. After this time, two drops of triethylamine are added to the solution under an N2 counterflow, and the resulting mixture is stirred for 5 min before being filtered over a short alumina column (elution with CH2Cl2). After evaporation of all volatiles, the crude product is purified by flash column chromatography to give the multisubstituted silane 3.

References


Application
Metal-Free Hydrogenation of Ketone by Frustrated Lewis Pairs (FLPs)

T2313

Typical procedure (R, R’ = n-Pr): 4-Heptanone (1.00 g, 8.76 mmol) is weighed into a 125 mL reactor. Subsequently, B(C6F5)3 (0.224 g, 0.43 mmol) dissolved in Et2O (14.3 mg, 20 mL, 0.19 mol) is added to the reactor. The reactor is sealed and attached to a hydrogen gas line. The flask is purged ten times at 15 atm with hydrogen gas. The reactor is then pressurized with 60 atm hydrogen gas and placed in an oil bath for 12 h at 70 °C. The reactor is slowly vented and all the volatiles are collected by vacuum distillation while cooling the collected distillate with liquid nitrogen. The solvent is removed by applying a gentle stream of N2 gas to give 4-heptanol (886 mg, 87% yield, and 99 % conversion determined by 1H NMR).

References


Application
Metal-Free Hydrogenation of N-Phenyl Aromatic Rings

Typical procedure (Entry 1): A 25 mL glass bomb equipped with Teflon screw cap is charged with a solution of B(C6F5)3 (37.9 mg, 1 eq.) and N-isopropylaniline (10.0 mg, 0.074 mmol) in toluene (1 mL). The reaction tube is degassed three times through a freeze-pump-thaw cycle on the vacuum/H2 line and filled with H2 (4 atm) at -196 °C. The reaction bomb is placed in a 110 °C oil bath for 36 h. The toluene is removed under reduced vacuum to yield a white precipitate. The product is washed with pentane (2 x 2 mL) and dried under reduced pressure to give [iPrNH2Cy][HB(C6F5)3] (93 %).

References


Application
Metal-free Hydrogenation of Imines Catalyzed by B(C6F5)3

Typical Procedure: In a glovebox, B(C6F5)3 (18.2 mg, 0.0355 mmol, 20 mol%) is dissolved in dry diisopropylamine (2.5 mL, 1.8 g, 17 mmol) and the solution is added to N-benzylidene-tert-butylamine (28.7 mg, 0.177 mmol, 1 eq.). The resulting solution is transferred to a 25 mL bomb with a sealable Teflon tape and magnetic stirbar. The reaction vessel is sealed, removed from the glovebox and stirred at 100°C for 24 h after which it is cooled to room temperature. The reaction mixture is quenched by the addition of silica followed by elution through a short silica column. The filtrate is concentrated in vacuo to give the desired product.

References


PubMed Literature


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