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

Tris(pentafluorophenyl)borane

Purity: >98.0%(NMR)

Synonyms:

Product Documents:

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1G	NT$6,680	≥100	28	Contact Us	Shipping Simulation
5G	NT$25,160	≥40	10	It can be shipped in about 2 weeks after ordering	Shipping Simulation

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General Information plus

Product Number	T2313
Purity / Analysis Method	>98.0%(NMR)
Molecular Formula / Molecular Weight	C₁₈BF₁₅ = 511.98
Physical State (20 deg.C)	Solid
Storage Temperature	Frozen (<0°C)
Store Under Inert Gas	Store under inert gas
Condition to Avoid	Hygroscopic,Heat Sensitive
Packaging and Container	1G-Glass Bottle with Plastic Insert (View image)
CAS RN	1109-15-5
Reaxys Registry Number	2931347
PubChem Substance ID	87558752
Merck Index (14)	9755
MDL Number	MFCD00269813

Specifications & Properties plus

Safety & Regulations plus

Applications & Literature plus

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

B(C₆F₅)₃‑Catalyzed Regioselective Deuteration of Electron-Rich Aromatic and Heteroaromatic Compounds
- W. Li, M.-M. Wang, Y. Hu, T. Werner, Org. Lett. 2017, 19, 5768.

Application

High Throughput Sequence-controlled Oligosiloxane Synthesis

References

By-Product-Free Siloxane-Bond Formation and Programmed One-Pot Oligosiloxane Synthesis
- K. Matsumoto, K. V. Sajna, Y. Satoh, K. Sato, S. Shimada, Angew. Chem. Int. Ed. 2017, 56, 3168

Application

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

References

Heterolytic dihydrogen activation with the 1,8-bis(diphenylphosphino)naphthalene/B(C₆F₅)₃ pair and its application for metal-free catalytic hydrogenation of silyl enol ether
- H. Wang, R. Fröhlich, G. Kehr, G. Erker, Chem. Commun. 2008, 5966.

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

Formal SiH₄ chemistry using stable and easy-to-handle surrogates
- A. Simonneau, M. Oestreich, Nature Chem. 2015, 7, 816.

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

J. M. Farrell, Z. M. Heiden, D. W. Stephan, Organometallics 2011, 30, 4497.

PubMed Literature

Articles/Brochures

Olefin Polymerization Catalysts

Monosilane (SiH4) Surrogate with Ease of Handling

TCIMAIL

[Product Highlights] Deuteration of Aromatic and Heteroamomatic Compounds Catalyzed by Tris(pentafluorophenyl)borane
[Product Highlights] A Bisphosphine Usable for Metal-free Hydrogenations
[Research Articles] High Throughput Sequence-controlled Oligosiloxane Synthesis
[Research Articles] Tri(cyclohexa-2,5-dien-1-yl)silane: A Stable and Easy-to-handle Surrogate of Monosilane (SiH4)
[Research Articles] Metal-Free Hydrogenation of Ketone by Frustrated Lewis Pairs (FLPs)
[Research Articles] Metal-Free Hydrogenation of N-Phenyl Aromatic Rings
[Research Articles] Metal-Free Hydrogenation of Imines Catalyzed by B(C6F5)3

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Appearance	White to Gray to Brown powder to crystal
Purity(NMR)	min. 98.0 atom%
Water	max. 1.0 %

Melting Point	128 °C
Maximum Absorption Wavelength	306 nm (Toluene)
Solubility (soluble in)	Toluene

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. P305 + P351 + P338 : IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P362 + P364 : Take off contaminated clothing and wash it before reuse. P332 + P313 : If skin irritation occurs: Get medical advice/ attention.

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

Tris(pentafluorophenyl)borane

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

Tris(pentafluorophenyl)borane

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