Octyltriethoxysilane

​Octyltriethoxysilane, also known as triethoxy(octyl)silane, is an organosilane compound with the chemical formula C₁₄H₃₂O₃Si and a molecular weight of 276.49 g/mol. It is a colorless, transparent liquid characterized by an alcohol-like odor. The compound has a boiling point of approximately 98 °C at 4 mmHg and a melting point around -40 °C. Its density ranges between 0.8740 and 0.8840 g/cm³ at 20 °C, and it possesses a refractive index of about 1.417 at 20 °C. Octyltriethoxysilane is insoluble in water but can hydrolyze upon exposure to moisture, producing ethanol and octylsilanetriol.

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, 90percent) and (EtO)4Si(0.05 mmol, 5percent). 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, 85percent). 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.To an NMR tube equipped with a Teflon valve were addedNi(acac)2 (13.0 mg, 0.05 mmol), 1-octene (11.3 mg, 0.1 mmol), (EtO)3SiH (16.0 mg, 0.1 mmol), and THF-d8 (0.5 mL). After theaddition of NaBHEt3 (1.0 M in THF, 50 mL, 0.05 mmol) to this solutionat room temperature, the reaction was followed by 1H NMR.After 2 h, the reaction did not proceed and only the signalsassignable to the starting materials [1-octene and (EtO)3SiH] weredetected by 1H NMR. The reaction was further followed at 50 °C for14 h, and formation of (EtO)3(nOct)Si (54percent) as well as (EtO)4Si (8percent)and (EtO)3SiOSi(OEt)3 (7percent) was observed. During the reaction, nohydride signals were detected in the high field region (δ 0 to -30 ppm).In a 500-ml three-necked flask, octene (1.25 mol) was added, and Catalyst 1 (1.25 mmol) prepared in was slowly heated to 90°C under a nitrogen atmosphere.While stirring, triethoxyhydrosilane (1.5 mol) was added dropwise through the dropping funnel. The dropwise addition time was 0.5 hours, the reaction temperature was maintained, and the stirring reaction was continued for 5 hours.After cooling to room temperature, the corresponding fractions were collected by distillation under reduced pressure. The conversion of octene was 94.7percent as determined by GC-MS.The yield of the β adduct 1-triethoxysilyloctane was 100percent.In a 500-ml three-necked flask, octene (1.25 mol) was added, and Catalyst 1 (1.25 mmol) prepared in was slowly heated to 90°C under a nitrogen atmosphere.While stirring, triethoxyhydrosilane (1.5 mol) was added dropwise through the dropping funnel. The dropwise addition time was 0.5 hours, the reaction temperature was maintained, and the stirring reaction was continued for 5 hours.After cooling to room temperature, the corresponding fractions were collected by distillation under reduced pressure. The conversion of octene was determined to be 94.3percent by GC-MS.The yield of the β adduct 1-triethoxysilyloctane was 100percent.o a scintillation vial equipped with a stir bar in a nitrogen filled glovebox was added (Reactions were carried out in a three-necked flask with a magnetic stirrer and a reflux condenser with an attached drying system on the upper condenser. Olefin and platinum catalyst were stirred at the reaction temperature for 30 min before triethoxysilane which was added at a constant speed. The reaction mixture was heated at the reaction temperature within the stipulated time and then catalyst was separated from the raw product by decantation. After the removal of the raw product, a new portion of substrates was added and the reaction was repeated under the same conditions. Gas chromatography was employed to follow the course of the reaction by the appearance of product. All hydrosilylation products were characterized by General procedure: All catalysis reaction operations were performed in a 10 mL flat-bottomed tube without protection from air. The alkene (4.0 mmol) and the requisite amount of catalyst were placed in a dried tube and the reaction mixture was stirred for 5 min. Thereafter, the silane (4.4 mmol) was added and the resulting mixture was heated and stirred for the requisite time and then cooled to room temperature. The product phase was separated by decantation and the conversion of the alkene and the selectivity were determined by GC–MS analysis on an Agilent 26890N/59731 apparatus equipped with a DB-5 column (30 m × 2.5 mm × 0.25 μm). General procedure: Hydrosilylation was carried out in a three-necked flask with amagnetic stirrer and a reflux condenser with an attached dryingsystem on the upper condenser. The olefin and platinumcomplex were stirred at the setting temperature for 30 min atfirst. Then the triethoxysilane was added at a constant speed.The reaction mixture was maintained at the reaction temperaturewithin the stipulated time. After the reaction, the catalystwas separated from the raw product by centrifugation. A newportion of substrates was added and the reaction was repeatedunder the same conditions. Gas chromatography was employedtofollowthe course of the reactionby the appearance of product.General procedure: All the catalytic reactions were performed in a 10 mLat-bottomed tube without protection from air. The alkene(4.0 mmol) and the requisite amount of catalyst were placed ina dried tube and the reaction mixture was stirred for 5 min.Thereafter, the silane (4.4 mmol) was added and the resulting mixture was heated and stirred for the requisite time andthen cooled to room temperature. The product phase was separated by decantation and the alkene conversion and selectivity of the reaction were determined by GC-MS analysis on anAgilent 26890N/59731 apparatus equipped with a DB-5 column(30 m × 2.5 mm × 0.25 mm).A 50 mL Schlenk flask equipped with a stir bar was charged with 1-octene (112 mg, 1 mmol) and triethoxysilane (164 mg, 1 mmol) in the glove box. The flask was sealed with a glass stopper and transferred out of the box. (terpy)Co(PhGeneral procedure: Example 16: THF solution (5 mL) of Nickel complex compound (0.005mmol) shownin Table 2 was placed in vial, then for the nickel complex compound, 20-foldmolar amount 1-octene, hydrosilanes shown in Table 2, equimolar amount hydridereducing agent were added sequentially to initiate the reaction. After a lapseof time shown in Table 2, the reaction solution was exposed to air to terminatethe reaction (the color of the solution turned colorless.), the yield of thefollowing product was quantified by GC analysis. The results are shown in Table2.In a glove box, 1-octene (112 mg, 1 mmol) and triethoxysilane (164 mg, 1 mmol) were weighed into a vial equipped with a stir bar. Purple (terpy)Co(Me

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Molecular Weight:276.49
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:13
Exact Mass:276.21207141
Monoisotopic Mass:276.21207141
Topological Polar Surface Area:27.7
Heavy Atom Count:18
Complexity:159
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes