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CAS No. : | 89171-23-3 | MDL No. : | MFCD06797410 |
Formula : | C24BF20K | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | GYBHRIJOPWTIKA-UHFFFAOYSA-N |
M.W : | 718.13 | Pubchem ID : | 23693577 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P403+P233-P405-P501 | UN#: | |
Hazard Statements: | H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | In hexane; dichloromethane; toluene at 25℃; for 1h; | EXAMPLE Toluene (0.35 g) was added to 0.72 g of KB(C6F5)4, which resulted in formation of a wet cake. The wet cake could not be stirred. Addition of CH2Cl2 (2.1 g) to the wet cake resulted in a slurry which was stirrable. Trityl chloride (Ph3CCl; 0.33 g, 120 mol %) was added slowly with stirring into the slurry, forming deep-red Ph3CB(C6F5)4. The slightly exothermic reaction was completed in about 1 minute. KCl was formed as a side product. The KCl was collected by filtration; the filter cake was rinsed with 2.0 g of CH2Cl2. The resultant solution of Ph3CB(C6F5)4 weighed 4.5 g, for a concentration of 20 wt %. Evaporation of 1.0 g of CH2Cl2 gave a 26 wt % of Ph3CB(C6F5)4. [0024] Hexane (4.0 g) was added slowly to the Ph3CB(C6F5)4/CH2Cl2 solution at 25° C. with fast stirring. A red oily layer was observed at first; this solidified within 10 minutes and coated the flask wall. After stirring for 1 hour at 25° C., all of the solids came off the flask wall to form fine yellow Ph3CB(C6F5)4 product. This yellow solid was collected by filtration on a coarse frit and then rinsed once with hexane (3.0 g). NMR analysis (internal standard method) of purge-dried B4 solids showed a 99+% purity. The yield was at least 89%. |
82% | In dichloromethane | |
76% | In dichloromethane for 1h; Inert atmosphere; Glovebox; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | In dichloromethane at 0℃; for 0.25h; | A A 50 mL Schlenk is charged with precursor complex 1 (20 mmol). CH2Cl2 (10 mL) is added to form a clear brown solution. A solution of potassium tetrakis(pentafluorophenyl)borate (20 mmol) in CH2Cl2 (5 mL) is added by syringe at 0° C. to form a brown solution with a white precipitate. The reaction mixture is stirred at 0° C. for 15 min. The mixture is filtered to remove KCl, and the product is dried under vacuum to afford a brown solid, which is purified by crystallization in CH2Cl2 (1 mL) at -80° C. The experiment should afford a brown solid(yield: 85%). NMR spectra should reveal that the product is Catalyst 5. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | In acetonitrile for 1h; Glovebox; | 1 Comparative Example 1 (0064) An experiment was performed in a glove box while minimizing light exposure. 0.19 g (1.12 mmol) of AgNO3 was dissolved in 5 ml of an anhydrous acetonitrile solution and then slowly added to 10 ml of anhydrous acetonitrile in which 1.00 g (1.39 mmol) of K[B(C6F5)4] (Alfa Aesar Co.) was dissolved. After 1 hour, all solvents were removed under a reduced pressure. Then, the resultant product was dissolved in dichloromethane and KNO3 salt which was a by-product was removed by filtering. Solvents were partially removed under a reduced pressure, and hexane was added thereto and crystallization was performed at -30° C. to produce 0.84 g of Ag[B(C6F5)]4 (77% yield). |
64% | In diethyl ether; water AgNO3 in H2O was added to a soln. of KB(C6F5)4 in diethyl ether, stirredvigorously for 10 min; the organic phase was dried with Na2SO4, the ether was removed in vac.; | |
In not given (Ar); |
In acetonitrile at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In chloroform; water at 20℃; for 7h; | 3 Synthesis Example 1 Pentafluorobenzene) borate (manufactured by Wako Pure Chemical Industries, Ltd.) was used instead of potassium tetrafluoroborate,In the same manner as in Synthesis Example 1,Synthesis of specific coloring compounds,And by measuring 1H-NMR (solvent: deuterated chloroform)The target compound was confirmed.This was compound C.The1H-NMR spectrum of Compound C was as follows. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91.5% | In ethanol at 25℃; for 24h; | 5 General procedure: 1.000 g of the compound (A) represented by the following structural formula,1.260 g of 1-naphthylmethyl chloride,4.656 g of potassium tetrakis (pentafluorophenyl) borate salt,And 2.00 g of ethanol were charged in a 50 ml three-necked flask,Stirring at 25 ° C for 24 hours,Reaction was carried out.After completion of the reaction,After adding 10 g of ethyl acetate,After stirring for a while,Thereafter, the precipitated KCl was removed by filtration,The filtrate was recovered. Since crude crystals were obtained by distilling off the solvent from the filtrate,After washing the crude crystals with pure water,Dried under reduced pressure,Recrystallization with ethanol / hexane gave a white crystal of the sulfonium compound (1) in a yield of 82.3%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91.56% | In dichloromethane at 25 - 30℃; for 2h; | 4 Example 4 Synthesis of N,N-di(octadecyl)anilinium tetrakis(pentafluorophenyl)borate In a 5 L glass reactor, 351 g of potassium pentafluorobenzeneborate and 1668 g of dichloromethane were added, and the mixture was stirred at room temperature (25 ° C) for 30 min. 292 g of N,N-di(octadecyl)aniline was added, and the reaction was stirred for 2 hours under the conditions of a temperature of 25 to 30 ° C in the autoclave. The reaction was stopped, 20 g of diatomaceous earth was added, and stirred for 10 min. After removing the insoluble solid by vacuum filtration, the organic phase filtrate was evaporated under reduced pressure to remove most of the solvent dichloromethane. 290 g of n-heptane was added, and the low boiling point dichloromethane was further distilled off under reduced pressure. The residue was allowed to stand to precipitate a large amount of solid, which was filtered in vacuo to give a crude solid. The crude product was dried under vacuum at 50 ° C for 10 hours to give an off-white solid.N,N-di(octadecyl)anilinium tetrakis(pentafluorophenyl)borate 572 g (molar yield 91.56%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | In dichloromethane at 20℃; Schlenk technique; | 1 -(3,5-Diphenyl-4-hydroxyphenyl)-2,4,6-triphenylpyridin-1 -ium B[C6F5]4e 1 -(3,5-Diphenyl-4-hydroxyphenyl)-2,4,6-triphenylpyridin-1 -ium tetrafluoro- borate (225 mg, 0.352 mmol) was dissolved in 10 mL CH2CI2. To the yellow solution KB(C6F5)4 (253 mg, 0.352 mmol, 1 equiv.) was added as a solid. The suspension was stirred overnight at room temperature. A white precipitate was filtered through a pad of celite. After removing the solvent in vacuo, the residue was taken up in 5 mL of CH2CI2 and filtered over a pad of silica. CH2CI2 was removed in vacuo. The product was obtained as yellow foam. After stirring in 3 mL diethyl ether an off white solid precipitated and was filtered off. (390 mg, 85%). (0272) [00168] 1H-NMR (400 MHz, CDCI3): d = 8.24, 7.82, 7.68, 7.59, 7.53, 7.45, 7.39, 7.31 , 7.04, 6.85, 5.63 ppm; 13C-NMR (101 MHz, CDCI3): d = 158.3, 157.5, 150.7, 149.4, 147.0, 139.4, 137.5, 136.9, 135.1 , 134.5, 133.7, 132.9, 132.3, 131 .4, 130.7, 130.4, 130.2, 129.4, 129.3, 129.1 , 128.9, 128.8, 128.1 , 125.7 ppm; 19F-NMR (376 MHz, CDCI3): d = -132.50, -162.94, -166.81 ppm. Elemental analysis (%) calcd. for C69H4OBF2ON02: C, 63.46; H, 3.09; N, 1 .07. Found: C, 63.22; H, 2.794; N, 1 .34. |
85 % | In dichloromethane at 20℃; Schlenk technique; | 1 -(3,5-Diphenyl-4-hydroxyphenyl)-2,4,6-triphenylpyridin-1 -ium B[C6F5]4e 1 -(3,5-Diphenyl-4-hydroxyphenyl)-2,4,6-triphenylpyridin-1 -ium tetrafluoro- borate (225 mg, 0.352 mmol) was dissolved in 10 mL CH2CI2. To the yellow solution KB(C6F5)4 (253 mg, 0.352 mmol, 1 equiv.) was added as a solid. The suspension was stirred overnight at room temperature. A white precipitate was filtered through a pad of celite. After removing the solvent in vacuo, the residue was taken up in 5 mL of CH2CI2 and filtered over a pad of silica. CH2CI2 was removed in vacuo. The product was obtained as yellow foam. After stirring in 3 mL diethyl ether an off white solid precipitated and was filtered off. (390 mg, 85%). (0272) [00168] 1H-NMR (400 MHz, CDCI3): d = 8.24, 7.82, 7.68, 7.59, 7.53, 7.45, 7.39, 7.31 , 7.04, 6.85, 5.63 ppm; 13C-NMR (101 MHz, CDCI3): d = 158.3, 157.5, 150.7, 149.4, 147.0, 139.4, 137.5, 136.9, 135.1 , 134.5, 133.7, 132.9, 132.3, 131 .4, 130.7, 130.4, 130.2, 129.4, 129.3, 129.1 , 128.9, 128.8, 128.1 , 125.7 ppm; 19F-NMR (376 MHz, CDCI3): d = -132.50, -162.94, -166.81 ppm. Elemental analysis (%) calcd. for C69H4OBF2ON02: C, 63.46; H, 3.09; N, 1 .07. Found: C, 63.22; H, 2.794; N, 1 .34. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | Stage #1: 4-(isopropylphenyl)(4-methylphenyl)[tetrakis(pentafluorophenyl)borato]-λ3-iodane With sodium azide In ethanol at 80℃; for 12h; Stage #2: potassium chloride In water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | In dichloromethane at 20℃; for 16h; | 2.9. Synthesis of complex 4 A CH2Cl2 solution (1 mL) of K[B(C6F5)] (22 mg, 30.6 μmol, 1 eq) wasadded dropwise to a stirred CH2Cl2 solution (3 mL) of complex 3 (16.5mg, 30.6 μmol, 1 eq) at room temperature, and the resulting mixture wasstirred for 16 h. After evaporation to dryness, washing with pentane (2× 5 mL) and drying under vacuum, a dark powder was isolated (33.4mg, 90% yield). Anal. Calcd for C43H15BCoF20NO2S2 (1091.43): C,47.32; H, 1.39; N, 1.28%. Found: C, 47.47; H, 1.62; N, 1.17%. MS (ESI):m/z 412.0 [M - B(C6F5)]+. FTIR: νmax(solid)/cm 1: 1644w, 1578w,1514m, 1456vs, 1397sh, 1373w, 1303w, 1266m, 1241sh, 1083s, 975vs,885w, 851w, 774m, 768sh, 755s, 725w, 683m, 661m, 610w, 601w,573m, 465w, 438m. 1H NMR (300 MHz, d6-acetone): δ (ppm) 5.02 (4H,s, CH2), 6.42 (2H, d, 3J = 8.4 Hz, Harom), 6.54 (2H, pseudo t, 3J = 7.5 Hz,Harom), 6.86 (2H, pseudo t, 3J = 7.8 Hz, Harom), 7.70 (4H, d, 3J = 7.5 Hz,Harom), 7.91 (1H, t, 3J = 7.8 Hz, Harom). 19F{1H} NMR (282 MHz, d6-acetone): δ (ppm) 133.0 (d), 164.4 (t), 168.0 (t). 11B{1H} NMR(128 MHz, d6-acetone): δ (ppm) = -16.6. UV-Vis: λmax(CH2Cl2)/nm: 401(ε/dm3 mol 1 cm 1: 1 700). |