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CAS No. : | 775-12-2 | MDL No. : | MFCD00003002 |
Formula : | C12H12Si | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | BPYFPNZHLXDIGA-UHFFFAOYSA-N |
M.W : | 184.31 | Pubchem ID : | 6327659 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 0.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 60.7 |
TPSA : | 0.0 Ų |
GI absorption : | Low |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -4.9 cm/s |
Log Po/w (iLOGP) : | 2.54 |
Log Po/w (XLOGP3) : | 3.55 |
Log Po/w (WLOGP) : | 0.81 |
Log Po/w (MLOGP) : | 3.88 |
Log Po/w (SILICOS-IT) : | 2.28 |
Consensus Log Po/w : | 2.61 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.77 |
Solubility : | 0.0313 mg/ml ; 0.00017 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.24 |
Solubility : | 0.107 mg/ml ; 0.000582 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -5.02 |
Solubility : | 0.00177 mg/ml ; 0.00000959 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 3.55 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280 | UN#: | N/A |
Hazard Statements: | H315 | Packing Group: | N/A |
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 |
---|---|---|
92.6% | With copper(l) iodide; copper dichloride In diethyl ether at 20℃; for 2 h; Inert atmosphere | A mixture of 18.44g (0.1mol) of Ph2SiH2, 26.9g (0.2mol) of anhydrous CuCl2, 0.92g (0.0048mol) of anhydrous CuI, 80g of ceramic spheres and 40mL of diethyl ether was stirred with a mechanical stirrer at 400rpm at room temperature for 2h. The mixture was filtered, and the filtrate was concentrated. The residue was distilled under reduced pressure to give Ph2SiHCl (20.24g, 92.6percent) as a colorless liquid. Bp. 117°C (210pa): 1H NMR: δ 5.82 [s, 1H, SiH], 7.47–7.76 [m, 10H, Si(C6H5)]. 13C NMR: δ 128.36, 131.10, 131.85, 134.52 [m, 12C, Si(C6H5)]. 29Si NMR: δ−5.94 [s, 1Si, Ph2SiHCl]. |
92.6% | With copper(l) iodide; copper dichloride In diethyl ether at 20℃; for 4 h; Inert atmosphere | In three bottles, through nitrogen dehumidification. 18.44 g of diphenylsilane (Ph2SiH2), 26.9 g of copper chloride (CuCl2), 0.92 g of cuprous chloride (Cul) and 10 g of ceramic balls were added, and the reaction was stirred for 4 h at room temperature. The silane conversion was measured by 29 Si NMR. The air filter was separated and the solid by-products were washed. The filtrate was combined and distilled under reduced pressure to obtain 20.24 g of diphenylchlorosilane (Ph2SiHCl) with a yield of 92.6percent and a purity of 99.9percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With potassium hexamethylsilazane In neat liquid at 30℃; for 2 h; Schlenk technique; Inert atmosphere | General procedure: Catalyzed CDC reactions were carried out using the following standard protocol. In the glove box, the chosen pre-catalyst (0.05 mmol) was loaded into a Schlenk tube, and subsequently the alcohol (n x 0.05 mmol, n equiv.) followed by silane (n' x 0 0.05 mmol, n' equiv.) were added. The reaction mixture was stirred at the desired temperature (30°C), which was controlled by an oil bath. After the required period, the reaction was quenched by adding CDCl3 to the mixture. Substrate conversion was monitored by examination of the 1H NMR spectrum of the reaction mixture and comparing relative intensities of resonance characteristics of the substrates and products. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84.8% | With lithium aluminium tetrahydride; calcium hydride; zirconium(IV) oxide; In diethylene glycol dimethyl ether; at 110℃; for 21h;Inert atmosphere; | The 250 mL four-neck round bottom flask was dried, connected to a mechanical stirrer, a spherical condenser tube, a constant pressure funnel and a gas guiding device, and vacuum was used to replace the nitrogen gas three times, while the hot air gun was baked to remove the attached water vapor.Under a nitrogen atmosphere, 9.3 g (0.22 mol) of CaH2, 0.38 g (0.01 mol) of lithium aluminum hydride, 25 mL of diethylene glycol dimethyl ether solvent, and 40 g of ZrO 2 ceramic microspheres (phi = 0.90 mm) were added to the reaction flask.41.5 mL (0.2 mol) of Ph2SiCl2 was added to the constant pressure funnel, and slowly added dropwise to the reaction flask under mechanical stirring.After the completion of the dropwise addition, the mixture was heated to 110 C and reacted for 21 hours to obtain the product Ph 2 SiH 2 .According to the integral area of the 1H-NMR spectrum (Fig. 3) of the reaction system, the conversion of the product was 84.8%. |
75% | With lithium hydride; In diethylene glycol dimethyl ether; at 0.7℃; for 1.5h;Inert atmosphere; | LiH (3.78 g, 0.48 mol) was placed in a three-necked flask and thoroughly dried diglyme wasadded as solvent. The diglyme/LiH suspension was carefully scaled from oxygen/air by degassing the suspension in vacuo and refilling with gaseous nitrogen to establish inert conditions. Then Ph2SiCl2 (56.46 g, 0.22 mol) was slowly added over a dropping funnel and reduction started after an induction period of 1 .5 hours by self-heating to about 70 C. After completion the reaction mixture cooled down to r.t. and was stirred for 18 hours. Afterremoval of LiCI by filtration under inert conditions Ph2SiH2 was separated from diglyme by fractional distillation at about 110-178 C under reduced pressure (about 0.1-32 mbar) to give30.59 g Ph2SiH2 (0.17 mol, 75 %). |
46% | With sodium tetrahydroborate; In acetonitrile; at 20℃; for 0.5h;Inert atmosphere; | After replacing the interior of a 7 mL test tube equipped with a stirring bar with nitrogen gas,Under nitrogen flow,In this test tube,0.25 mL of acetonitrile as a reaction solvent,As a reducing agent, sodium borohydride (NaBH 4, ReagentPlus (registered trademark), manufactured by Sigma-Aldrich Japan Co.,Purity 99%) 37.8 mg (1.0 mmol)To prepare a suspension.To this suspension,51.8 mg (0.25 mmol) of dichlorodiphenylsilane (Ph 2 SiCl 2) was dropped using a microsyringe,The reaction was allowed to proceed for 30 minutes while stirring at room temperature.After the reaction,Acetonitrile was distilled off,To the obtained product (mixture), 5 mL of n-hexane was added under the atmosphere,Filtered using a silica pad in an argon atmosphere glove box,By drying,21.3 mg (0.116 mmol) of diphenylsilane (Ph 2 SiH 2) was isolated.The yield of diphenylsilane was 46% (NMR yield 56%). |
With lithium aluminium tetrahydride; In diethyl ether; at 0℃; | General procedure: The preparation of all hereby-investigated arylsilanes was based on a reaction of the precursor aryl chlorosilanes with lithium aluminiumhydride (LiAlH4) in Et2O at 0C. Phase separation with diluted, de-gassed sulphuric acid, removal of salts over aqueous, degassed sodium tartrate solution and evaporation of the solvent resulted in the colourless hydride species. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With potassium hexamethylsilazane; In neat liquid; at 30℃; for 2h;Schlenk technique; Inert atmosphere; | General procedure: Catalyzed CDC reactions were carried out using the following standard protocol. In the glove box, the chosen pre-catalyst (0.05 mmol) was loaded into a Schlenk tube, and subsequently the alcohol (n x 0.05 mmol, n equiv.) followed by silane (n' x 0 0.05 mmol, n' equiv.) were added. The reaction mixture was stirred at the desired temperature (30C), which was controlled by an oil bath. After the required period, the reaction was quenched by adding CDCl3 to the mixture. Substrate conversion was monitored by examination of the 1H NMR spectrum of the reaction mixture and comparing relative intensities of resonance characteristics of the substrates and products. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With potassium hexamethylsilazane; In neat liquid; at 60℃; for 2h;Schlenk technique; Inert atmosphere; | General procedure: Catalyzed CDC reactions were carried out using the following standard protocol. In the glove box, the chosen pre-catalyst (0.05 mmol) was loaded into a Schlenk tube, and subsequently the alcohol (n x 0.05 mmol, n equiv.) followed by silane (n' x 0 0.05 mmol, n' equiv.) were added. The reaction mixture was stirred at the desired temperature (30C), which was controlled by an oil bath. After the required period, the reaction was quenched by adding CDCl3 to the mixture. Substrate conversion was monitored by examination of the 1H NMR spectrum of the reaction mixture and comparing relative intensities of resonance characteristics of the substrates and products. |
79% | With tert.-butylhydroperoxide; ammonium iodide; In water; at 80℃; for 24h; | General procedure: 70% aq TBHP (4.0 mmol) was added dropwise over 10 min to asolution of the appropriate silane (1.0 mmol) and NH4I (0.20mmol) in the appropriate alcohol (1 mL), and the mixture wasstirred at r.t. until the reaction was complete (TLC). The reactionwas then quenched with sat. aq Na2S2O3, and the mixture waswashed with brine, extracted with EtOAc, dried (Na2SO4), andconcentrated under vacuum. The crude product was purified bycolumn chromatography (silica gel, PE).Ethoxy(triphenyl)silane (3aa)Colorless liquid; yield: 280 mg (92%). |
77% | With C25H31FeIN2O; In acetonitrile; at 70℃; for 8h;Inert atmosphere; Schlenk technique; | General procedure: Acetonitrile (1 mL), (Cp*-NHCR)Fe(CO)I (1 mol%), alcohol (3 mmol), silane (1 mmol) were charged in a vial. The vial was tightly closed under a nitrogen atmosphere, and the mixture was heated at 70 C for 8-16 h depending on the silane and the alcohol. All volatiles were evaporated under vacuum, the residue was dissolved in CDCl3, and Ph2CH2 (1 mmol) was added to the mixture as an internal standard. The 1H NMR was measured at room temperature and the amount of the corresponding silylether produced was evaluated by the relative intensity of the signals of the product and internal standard. Isolation of the silylethers was carried out by removing all the volatiles under vacuum. The residue was diluted with hexanes (ca. 2 mL), loaded directly on to a silica gel column and chromatographed using hexane-acetone (10:1) as eluent to give the corresponding silylethers. The silylethers produced were identified by comparison of the NMR data with the reported data: PhSi(OEt)3, PhSi(OiPr)3 [18], Ph2Si(OEt)2 [19], PhSiH[OCH(Me)Ph]2 [20]. The obtained silylether Si(OEt)4 was compared with an authenticate sample (commercially available). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
>99% | With oxygen; In water; acetone; at 30℃; under 760.051 Torr; for 0.333333h; | General procedure: A typical reaction procedure for the oxidation of 1 to 2 using Au/HAP was as follows.Au/HAP (0.005 g, Au: 0.0415 mol%) was placed in a reaction vessel (50 cm3), followedby the addition of acetone (4 mL), water (0.1 mL), and 1 (1 mmol). The reactionmixture was vigorously stirred at 30 C under O2 atmosphere for 7 min. Au/HAP wasfiltered and the yield was determined by GC analysis. The product was isolated byKugelrohr distillation. |
90% | With silver; water; In acetone; at 20℃; for 2h; | General procedure: The preparation of dimethylphenylsilanol 2a was given as a representative example. Nanoporous silver (10 mg), acetone (1.5 mL), H2O(0.1 mL), and dimethylphenylsilane 1a (1 mmol) were added in a micro-reaction vial at room temperature. The mixture was stirred for 60 min until no bubbles emerged, and then the np-Ag was removed from the system. The reaction mixture was then concentrated by rotary evaporation and the residue was purified by column chromatography on silica gel using ethyl acetate/petroleum ether (60-90 C) (1:1) as eluent to give 2a. The recovered catalyst was washed with acetone and water and was reused without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94.1% | With copper(l) iodide; copper dichloride; In diethyl ether; at 20℃; for 4h;Inert atmosphere; | A mixture of 18.44g (0.1mol) of Ph2SiH2, 53.8g (0.4mol) of anhydrous CuCl2, 1.44g (0.0076mol) of anhydrous CuI, 120g of ceramic spheres and 60mL of diethyl ether was stirred with a mechanical stirrer at 400rpm at room temperature for 4h. The mixture was filtered, and the filtrate was concentrated. The residue was distilled under reduced pressure to give Ph2SiCl2 (23.8g, 94.1%) as a colorless liquid. Bp. 150C (210pa): 1H NMR: delta 7.49-7.83 [m, 10H, Si(C6H5)]. 13C NMR: delta 128.47, 131.87, 131.91, 134.11 [m, 12C, Si(C6H5)]. 29Si NMR: delta 5.41 [s, 1Si, Ph2SiCl2]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With sodium t-butanolate; In tetrahydrofuran; at 20℃; for 4h;Inert atmosphere; | Under an argon atmosphere, add 20 mg of heterogeneous catalyst, 1.0 mmol of 4-octyne, 1.2 mmol of <strong>[775-12-2]diphenylsilane</strong>, and 2.5 mL of tetrahydrofuran to a 25 mL branch tube with a magnetic stir bar, then add 40mg sodium tert-butoxide,The reaction was stirred at room temperature for 4 hours, and the solvent was removed in vacuo. The crude product was purified by column chromatography using petroleum ether as eluent to obtain a colorless liquid product with a yield of 67%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With magnesium oxide; In toluene; at 30 - 80℃; for 6h; | A mixture of 12.67 g (100.6 mmol) of <strong>[1785-61-1]1,3-diethynylbenzene</strong>, 2.56 g (25.1 mmol) of phenylacetylene, and 20.6 g (73 mmol) of diphenylsilane in solution in 100 ml of anhydrous toluene is dropwise introduced into a 1 liter three-necked flask placed under argon and containing 20 g (0.5 mmol) of magnesium oxide as a powder suspended in 100 ml of anhydrous toluene, is left with stirring at 30 C. for 2 hours, and then at 40 C. for 1 hour, and then at 50 C. for 1 hour, and then at 60 C. for 1 hour, then at 80 C. for 1 hour. The solution is then filtered, and the solvent is evaporated off. 27.5 g (80% yield) of a polymer is then collected, as an oil. [00143] The number average molecular weight of this compound is 1.312 for a weight average weight of 3.827 (polydispersity of 2.91). These weights were determined by GPC from a calibration with polystyrene. [00144] The viscosity of this polymer is 1.050 mPa.s at 130 C. and 650 mPa.s at 150 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With bis(tri-tertiary-butylphosphine)palladium(0); triethylamine In tetrahydrofuran at 20℃; for 48h; Inert atmosphere; | |
27% | With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; triethylamine In tetrahydrofuran at 20℃; for 48h; Inert atmosphere; Glovebox; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: Na / decalin 2: not given |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With oxygen; sodium t-butanolate; In tetrahydrofuran; at 20℃; for 1h; | To a scintillation vial equipped with a stir bar was added CuIPr (14.6 mg, 0.030 mmol), sodium tert-butoxide (11.5 mg, 0.12 mmol), and THF (5 mL). The reaction vessel was left open to air. The heterogeneous solution was stirred for 10 min before the addition of diphenyl silane (0.186 mL, 1.0 mmol). An immediate color change to bright yellow was observed and stirring was continued for 1 h, over which time the reaction solution darkened significantly. The reaction solution was then treated with charcoal, run through a plug of silica and celite, and recrystallized from dichloromethane and hexanes. The resultant highly crystalline white solid was isolated by filtration (0.25 mmol, 0.197 g, 100%). 1HNMR (CDCl3): 7.23 (16H, t, J = 7.33), 7.39 (8H, tt, J = 7.49), 7.53 (16H, dd, J = 7.33). 13C NMR (CDCl3): 127.63 (CH), 130.04 (C), 134.40 (CH). Anal Calcd for C48H40O4Si4: C, 72.68; H, 5.08. Found: C, 72.62; H, 5.00. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With sodium triethylborohydride; In tetrahydrofuran; at 20℃; for 0.0833333h;Inert atmosphere; | 20 C,Under nitrogen conditions,The CoX2-OIP complex (0.02 mmol) was added successively to a dry reaction tube,Tetrahydrofuran (2 ml), diphenylsilylhydride (1.0 mmol),Was injected with sodium triethylborohydride (0.06 mmol)Alkynes (1.0 mmol),And then stirred for 5 minutes to give the product by column chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With C25H33Cl2FeN3O; sodium triethylborohydride In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; Schlenk technique; Cooling with ice; stereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With [(N(C6H4N(CH3)2)2)Ni(OCH3)] In tetrahydrofuran at 20℃; for 6h; Inert atmosphere; Glovebox; Sealed tube; chemoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | General procedure: A typical procedure (Table 2, entry 1) is as follows. To a stirredsolution of Ni(acac)2 (1a) (1.3 mg, 0.005 mmol) in THF (5 mL) wasadded 1-octene (112 mg, 1.0 mmol) and (EtO)3SiH (164 mg,1.0 mmol) at room temperature. After the mixture was stirred for1 min, NaBHEt3 (1.0Min THF, 5 mL, 0.005 mmol) was added and theresulting mixture was heated at 50 C. The solution was stirred atthe same temperature, and the progress of the reaction wasmonitored by GLC. After completion of the reaction, mesitylene(60 mg, 0.50 mmol) was added as an internal standard to the reactionmixture. The GLC analysis of the resulting solution revealedthe formation of (EtO)3(nOct)Si (0.90 mmol, 90%) and (EtO)4Si(0.05 mmol, 5%). The solutionwas concentrated under vacuum, andthe residue was purified by gel permeation chromatography (GPC)using toluene as an eluent to give (EtO)3(nOct)Si (234 mg,0.85 mmol, 85%). The 1H, 13C{1H} and 29Si{1H} NMR spectra of theisolated compound are consistent with the reported data. A similarprocedurewas employed for the hydrosilylation using other silanesand 1,3-diene/alkenes/alkynes. These reactions were carried out atroom temperature except for the reactions, Table 2, entries 2-3.The 1H/13C NMR spectroscopic data for the new compounds aregiven in the supplementary data. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With C21H41N3NiP2; In N,N-dimethyl-formamide; at 20 - 60℃; for 36h;Sealed tube; | General procedure: [0182] Using tertiary amines, such as Et3N and DABCO (1,4-Diazabicyclo[2.2.2]octane) and imine, such as DBU (1,8-Diazabicyclo[5.4.0]undec-7-ene) as the catalysts led to no methanol product (Table 3, entries 4-6). The reaction worked well in polar aprotic solvents such as DMF, THF, and MeCN, with slower reaction rates in THF and MeCN (Table 3, entries 7 and 8), presumably because DIVIF can act as a Lewis base to help to activate silane and thus accelerate the reaction.28 No reaction was observed in CH2C12 and toluene (Table 3, entries 9 and 10). Further screening of catalyst loadings (Table 3, entries 11-16) revealed that diphenylsilane could be fully consumed with a catalyst loading as low as 0.02 mol% (Table 3, entry 16). The turnover number (TON) and turnover frequency (TOF) for hydride 2 as the catalyst in this reaction could reach 4900 and 136 h?, respectively (Table 3, entry 16), much higher than those of the (N-heterocyclic carbene) NHC catalysts.?4 To the best of our knowledge, this is the highest TON and TOF reported for the reduction of CO2 with silane to methanol.[0188] General procedures for reduction of CO2 to methanol: to a fresh vial was added nickel PN3P-pincer complex 2 (4.6 mg, 0.01 mmol), and 1.8 mL of DIVIF was introduced. The vial was sealed, and CO2 was introduced into the vial via a balloon. The reaction was allowed to stir for 30 mm at room temperature, after which diphenylsilane (0.19 mL, 1 mmol) was introduced. The reaction was quenched after 18 h by adding 2 equivalents of NaOH/H20 solution. It was stirred for another 24 h before an aliquot of isopropyl alcohol was added as an internal standard. An aliquot of 0.2 mL was removed from the sample and diluted with dichloromethane before the resulting mixture was subjected to GC analysis. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With sodium triethylborohydride; In tetrahydrofuran; at -30℃; for 0.0833333h;Inert atmosphere; | -30 C,Under nitrogen conditions,The CoX2-OIP complex (0.02 mmol) was added successively to a dry reaction tube,Tetrahydrofuran (2 ml),Diphenylsilyl hydride (1.0 mmol),Was injected with sodium triethylborohydride (0.06 mmol)Alkynes (1.0 mmol),And then stirred for 5 minutes to give the product by column chromatography.White solid,85% yield.M.p .: 54 to 55 C. |
70% | With sodium t-butanolate; In tetrahydrofuran; at 20℃; for 4h;Inert atmosphere; | Under an argon atmosphere, add 10 mg of heterogeneous catalyst, 1.0 mmol of 2-ethynylthiophene, 1.0 mmol of <strong>[775-12-2]diphenylsilane</strong>, and 2.5 mL of tetrahydrofuran to a 25 mL branch tube with a magnetic stir bar,Then add 40mg sodium tert-butoxide,The reaction was stirred at room temperature for 4 hours, and the solvent was removed in vacuo. The crude product was purified by column chromatography using petroleum ether as the eluent to obtain a colorless liquid product with a yield of 70%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45.2%; 46.1% | With tris(pentafluorophenyl)borate; In neat (no solvent); at 20℃; for 24h; | In a glove box, 1-methylindole (13.1 g 0.1 mol) was weighed and B(C6F5)3 (0.01 mmol, 5.6 mg) was stirred well in a 30 mL reaction flask.When B(C6F5)3 was completely dissolved, Ph2SiH2 (9.2 g, 0.05 mol) was added, stirred for 24 h at room temperature, and 0.2 mL of the reaction solution was dissolved in deuterated benzene with a pipette.The conversion rate of the reaction was calculated to be 96.9% by integrating the integrated area of the raw material and product nitrogen methyl group on the nuclear magnetic proton spectrum.The yields of 3-(diphenylsilyl)-1-methylindole and 1-methyl porphyrin were 46.1% and 45.2%, respectively.Work-up method: The reaction mixture was poured into 300 mL of hexane, stirred for 30 minutes, and filtered to give a white solid,After being washed with (3 x 30 mL) hexane and suction drying, 12.76 g of 3-(diphenylsilyl)-1-methylhydrazine was obtained as a white solid.The filtrate was concentrated, and 5.36 g of 1-methyl porphyrin was isolated by column chromatography using hexane as an eluent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40.52%; 41.19%; 17.65% | With tris(pentafluorophenyl)borate; In benzene-d6; at 20℃; for 3.5h; | In the glove box, 1-methylindole (0.25 mmol) was added to the nuclear magnetic tube.Then 0.5 mL (1.0% eq or 5.0% eq) B(C6F5)3 in toluene solution was added.Silane (0.25 eq or 0.5 eq or 2.0 eq) is then added.After completion of the reaction at room temperature or 120 C., the reaction mixture was quenched with 0.5 mL of triethylamine.The mixture was further purified by flash column chromatography on silica gel using cyclohexane/triethylamine/tert-butyl methyl ether (100/10/1) as the eluent to afford the 3-position silanized product and the substituted porphyrin. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93.6% | With platinum(IV) oxide; In benzene; at 5 - 20℃; for 20h; | Under 5 C, a mixture of 18.4 g (0.10 mol) of diphenylsilane and 50mL of benzene is slowly added drop-wise into 100mL of a benzene solution containing 1.2 g of platinum dioxide and 26.2 g (0.22 mol) of <strong>[15411-43-5]3-vinylaniline</strong>, 20 C stirred reaction for 20h, the solvent is distilled off under reduced pressure, the residue is re-crystallized from ethyl lactate, obtained product as an off-white solid 39.5 g of diphenyl Bis (3-aminophenethyl) silane, Yield 93.6%, content 98.6%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83.3%; 8.8% | In dichloromethane-d2; at 20℃; for 0.166667h; | B(C6F5)3 (12.8 mg, 0.025 mmol) and 0.3 mL of CD2Cl2 were added to a J. Young-type nuclear magnetic tube.To the solution was added 0.1 mL of Ph2SiH2 (4.6 mg, 0.025 mmol) and 0.2 mL of 1-methyl porphyrin (3.3 mg, 0.025 mmol) in CD2Cl2, respectively, using a syringe.Mix evenly. After 10 minutes of reaction, the solution is colorless. Perform the nuclear magnetic test. From the nuclear magnetic proton spectrum.It can be clearly seen that the main product produced is C9H11N.PhSiH2.B(C6F5)3 (3e). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | General procedure: A typical procedure (Table 2, entry 1) is as follows. To a stirredsolution of Ni(acac)2 (1a) (1.3 mg, 0.005 mmol) in THF (5 mL) wasadded 1-octene (112 mg, 1.0 mmol) and (EtO)3SiH (164 mg,1.0 mmol) at room temperature. After the mixture was stirred for1 min, NaBHEt3 (1.0Min THF, 5 mL, 0.005 mmol) was added and theresulting mixture was heated at 50 C. The solution was stirred atthe same temperature, and the progress of the reaction wasmonitored by GLC. After completion of the reaction, mesitylene(60 mg, 0.50 mmol) was added as an internal standard to the reactionmixture. The GLC analysis of the resulting solution revealedthe formation of (EtO)3(nOct)Si (0.90 mmol, 90%) and (EtO)4Si(0.05 mmol, 5%). The solutionwas concentrated under vacuum, andthe residue was purified by gel permeation chromatography (GPC)using toluene as an eluent to give (EtO)3(nOct)Si (234 mg,0.85 mmol, 85%). The 1H, 13C{1H} and 29Si{1H} NMR spectra of theisolated compound are consistent with the reported data. A similarprocedurewas employed for the hydrosilylation using other silanesand 1,3-diene/alkenes/alkynes. These reactions were carried out atroom temperature except for the reactions, Table 2, entries 2-3.The 1H/13C NMR spectroscopic data for the new compounds aregiven in the supplementary data. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With n-butyllithium | 2.3. Monomer synthesis Synthesis and characterization of the silylated dialdehydemonomers (6 and 7) were reported in previous studies performed by our research group [9]. Briefly, the precursor bis(4-bromophenyl)di-R-silane (R = CH3 or Ph) were obtained from the reaction between 1,4-dibromobenzene and the respective diorgano-silane in presence of n-BuLi. Then, these derivatives reacted at 85 °C with 4-formylphenylboronic acid by using Pd(PPh3)2Cl2 as catalyst in a 1,4-dioxane-water potassium carbonate (2 M) solution. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1,10-Phenanthroline; zinc diacetate; In [D3]acetonitrile; at 80℃; under 1875.19 Torr; for 24h;Autoclave; Glovebox;Catalytic behavior; Kinetics; | Zn(OAc)2 (0.02mmol, 3.7 mg),phen (0.06mmol, 10.8 mg), CD3CN (1 mL), Ph2SiH2 (3mmol,552 mg) were added to an autoclave. The autoclave was sealedtightly, and filled with CO2 to 0.25MPa (initial pressure). After24 h reaction at 80 C, CO2 was released gently, and mesitylenewas added as an internal standard. The solution was then transferredto a J. Young NMR tube for NMR analysis. 1HNMR(400 MHz): 3.6 ppm for CH3OSiR3; 13C{1H}NMR (100 MHz):52 ppm for CH3OSiR3 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 79 %Spectr. 2: 50 %Spectr. | With Hexamethyldisiloxane; mono(trimethylphosphine)(diallyl ether)palladium(0) In benzene-d6 at 30℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | Stage #1: diphenylsilane With cobalt(III) acetylacetonate; triethylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In cyclohexane at 20℃; for 0.25h; Inert atmosphere; Schlenk technique; Stage #2: (4,4-dimethylthiochroman-6-yl)acetylene; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In cyclohexane at 20℃; for 24h; Inert atmosphere; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With [{(DIPP-nacnac)CaH(thf)}2]; In toluene; at 100℃; for 15h;Inert atmosphere; Schlenk technique; Sealed tube; | General procedure: In a nitrogen-filled glovebox, complex 1 (0.025 mmol), terminal alkyne (0.5 mmol)and silane (1.5 mmol) in toluene (2 mL) were loaded into a 25 mL Schlenk tube. Thistube was sealed, taken out of the glovebox, and put into an oil bath which had beenpreviously set to 100 oC. After completion of the reaction (monitored by 1H NMR), thereaction was quenched by opening to air, and the volatiles of the reaction mixture wereremoved under vacuum at room temperature. The residue was purified by columnchromatography on silica gel to provide alkynylsilane. |
Tags: 775-12-2 synthesis path| 775-12-2 SDS| 775-12-2 COA| 775-12-2 purity| 775-12-2 application| 775-12-2 NMR| 775-12-2 COA| 775-12-2 structure
[ 4519-17-9 ]
1,4-Bis(dimethyl(vinyl)silyl)benzene
Similarity: 0.84
[ 13183-70-5 ]
1,4-Bis(trimethylsilyl)benzene
Similarity: 0.77
[ 185626-73-7 ]
(3-Bromophenyl)triphenylsilane
Similarity: 0.63
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