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CAS RN: 1109-15-5 | Produkte #: T2313
Tris(pentafluorophenyl)borane
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Reinheit: >98.0%(NMR)
Synonyme
Produktdokumente:
| Einheit | Stückpreis | Belgien | Japan* | Menge |
Versandinformationen
|
|---|---|---|---|---|---|
| 1G |
€93.00
|
13 | 9 |
|
|
| 5G |
€362.00
|
10 | ≥100 |
|
*Lagerbestand in Belgien: Versand am selben Tag
*Lagerbestand in Japan: Bitte prüfen Sie die Versandsimulation für voraussichtliche Lieferzeiten. (ausgenommen regulierte Produkte und Trockeneissendungen)
| Artikel # | T2313 |
Reinheit / Analysenmethode 
|
>98.0%(NMR) |
| Summenformel / Molekülmasse | C__1__8BF__1__5 = 511.98 |
| Physikalischer Zustand (20 °C) | Solid |
| Lagerungstemperatur
|
Frozen (<0°C) |
| Unter Inertgas lagern | Store under inert gas |
| Zu vermeidende Bedingungen | Hygroscopic,Heat Sensitive |
| Verpackung und Behälter
|
1G-Glass Bottle with Plastic Insert (Bild ansehen) |
| CAS RN | 1109-15-5 |
| Reaxys Registrierungsnummer | 2931347 |
| PubChem-Stoff-ID | 87558752 |
| Merck-Index (14) | 9755 |
| MDL-Nummer | MFCD00269813 |
Spezifikation
| Appearance | White to Gray to Brown powder to crystal |
| Purity(NMR) | min. 98.0 atom% |
| Water | max. 1.0 % |
Eigenschaften
| Schmelzpunkt | 128 °C |
| Maximale Wellenlänge | 306 nm (Toluene) |
| Löslichkeit (löslich in) | Toluene |
GHS
| Piktogramm |
|
| Signalwort | Achtung |
| Gefahrenhinweise | H315 : Verursacht Hautreizungen. H319 : Verursacht schwere Augenreizung. |
| Sicherheitshinweise | P264 : Nach Gebrauch Haut gründlich waschen. P280 : Schutzhandschuhe/ Augenschutz/ Gesichtsschutz tragen. P302 + P352 : BEI BERÜHRUNG MIT DER HAUT: Mit viel Wasser waschen. P337 + P313 : Bei anhaltender Augenreizung: Ärztlichen Rat einholen/ ärztliche Hilfe hinzuziehen. P362 + P364 : Kontaminierte Kleidung ausziehen und vor erneutem Tragen waschen. P332 + P313 : Bei Hautreizung: Ärztlichen Rat einholen/ ärztliche Hilfe hinzuziehen. |
Verwandte Gesetze:
Transportinformationen:
| HS-Nr. (Import / Export) (TCI-E) | 2931900090 |
Anwendung
Deuteration of Aromatic and Heteroamomatic Compounds Catalyzed by Tris(pentafluorophenyl)borane
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
Anwendung
High Throughput Sequence-controlled Oligosiloxane Synthesis
References
- By-Product-Free Siloxane-Bond Formation and Programmed One-Pot Oligosiloxane Synthesis
Anwendung
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
Anwendung
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.
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
Anwendung
Metal-Free Hydrogenation of Ketone by Frustrated Lewis Pairs (FLPs)
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
- T. Mahdi, D. W. Stephan, J. Am. Chem. Soc. 2014, 136, 15809.
- Highlighted in Chem. Eng. News 2014, 92 (44), 8.
Anwendung
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
- 1)T. Mahdi, Z. M. Heiden, S. Grimme, D. W. Stephan, J. Am. Chem. Soc. 2012, 134, 4088.
- 2)D. W. Stephan, G. Erker, Angew. Chem., Int. Ed. 2010, 49, 46.
Anwendung
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 Literatur
Produktartikel
[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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