5283-66-9

Usage

Uses

Used in Catalyst Industry:
N-OCTYLTRICHLOROSILANE is used as a functionalizing agent for magnesium oxide (MnO2) and aluminium oxide (Al2O3) surfaces, which can then be employed as catalysts in the decomposition of ozone (O3) and nitrogen dioxide (NO2).
Used in Electronics Industry:
N-OCTYLTRICHLOROSILANE is used for the surface modification of silicon oxide (SiO2), which is utilized in the fabrication of pentacene organic field-effect transistors (OFETs). This application enhances the performance and efficiency of the transistors.
Used in Biotechnology and Material Science:
OTS functionalized wafers can be coated on enhanced green fluorescent protein (GFP) and anchor peptides-based films. This application is used to determine the thickness of the films, which is crucial in various biotechnological and material science research and applications.

Reactivity Profile

Chlorosilanes, such as N-OCTYLTRICHLOROSILANE, are compounds in which silicon is bonded to from one to four chlorine atoms with other bonds to hydrogen and/or alkyl groups. Chlorosilanes react with water, moist air, or steam to produce heat and toxic, corrosive fumes of hydrogen chloride. They may also produce flammable gaseous H2. They can serve as chlorination agents. Chlorosilanes react vigorously with both organic and inorganic acids and with bases to generate toxic or flammable gases.

Health Hazard

TOXIC; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death. Contact with molten substance may cause severe burns to skin and eyes. Reaction with water or moist air will release toxic, corrosive or flammable gases. Reaction with water may generate much heat that will increase the concentration of fumes in the air. Fire will produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

Fire Hazard

Combustible material: may burn but does not ignite readily. Substance will react with water (some violently) releasing flammable, toxic or corrosive gases and runoff. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapors may travel to source of ignition and flash back. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated or if contaminated with water.

Flammability and Explosibility

Notclassified

Safety Profile

A corrosive irritant to skin, eyes, and mucous membranes. Will react with water or steam to produce toxic and corrosive fumes. When heated to decomposition it emits toxic fumes of Cl-. See also CHLOROSILANES.

Purification Methods

Purify the silane by repeated fractionation using a 15-20 theoretical plate glass column packed with glass helices. This can be done more efficiently using a spinning band column. The purity can be checked by analysing for Cl (ca 0.5-1g of sample is dissolved in 25mL of MeOH, diluted with H2O and titrated with standard alkali). It is moisture sensitive. [Whitmore J Am Chem Soc 68 475 1946, El-Abbady & Anderson J Am Chem Soc 80 1737 1958, Beilstein 4 III 1907.]

InChI:InChI=1/C8H17Cl3Si/c1-2-3-4-5-6-7-8-12(9,10)11/h2-8H2,1H3

Upstream product

• 17049-49-9 octylmagnesium bromide 
• 592-99-4 4-octene 
• 111-66-0 oct-1-ene 
• 111-85-3 n-chlorooctane 
• 10026-04-7 tetrachlorosilane 
• 10025-78-2 trichlorosilane 
• 7642-04-8 cis-2-octene 
• 13389-42-9 trans-2-Octene 
• 14850-23-8 trans-4-Octene 
• 74-85-1 ethene 

Downstream Products

• 18866-37-0 tribenzyl-octyl-silane 
• 871-92-1 trihydrogeno(octyl)silane 
• 3069-40-7 n-octyltrimethoxysilane 
• 2943-75-1 triethoxy(octyl)silane 
• 3429-76-3 trimethyl-octyl-silane 
• 18416-07-4 dichloro(dioctyl)silane 
• 31176-12-2 n-octyltrihydroxysilane 
• 111-87-5 octanol 
• 302778-42-3 (4-fluorobenzyl)trichlorosilane 
• 770-10-5 benzyltrichlorosilane 
• 2504-64-5 1,2-bis(trichlorosilyl)ethane 
• 1873-92-3 allyldichloromethylsilane 
• 3937-28-8 allyldichlorosilane 
• 18171-50-1 1,3-bis(trichlorosilyl)propane 

Relevant academic research and scientific papers

Remarkable activity, selectivity and stability of polymer-supported Pt catalysts in room temperature, solvent-less, alkene hydrosilylations

A polystyrene-resin supported Pt catalyst displays higher conversion, remarkably improved selectivity and excellent recyclability relative to Speier's catalyst in the room temperature solvent-less hydrosilylation of oct-1-ene using trichlorosilane.

The Addition Rates of Dichloro- and Trichlorosilane to 2-Pentene and 1-Octene

When mixtures of dichloro- and trichlorosilane were added to 2-pentene and 1-octene in the presence of a solution of chloroplatinic acid, dichloro-silane added much more rapidly than trichlorosilane.But when each silane was added separately under identical conditions, trichlorosilane added much more rapidly than dichlorosilane to the same olefins.

PROCESS FOR THE STEPWISE SYNTHESIS OF SILAHYDROCARBONS

The invention relates to a process for the stepwise synthesis of silahydrocarbons bearing up to four different organyl substituents at the silicon atom, wherein the process includes at least one step a) of producing a bifunctional hydridochlorosilane by a redistribution reaction, selective chlorination of hydridosilanes with an ether/HCI reagent, or by selective chlorination of hydridosilanes with SiCI4, at least one step b) of submitting a bifunctional hydridochloromonosilane to a hydrosilylation reaction, at least one step c) of hydrogenation of a chloromonosilane, and a step d) in which a silahydrocarbon compound is obtained in a hydrosilylation reaction.

Hydrosilylation of alkenes catalyzed by Fe powder

A novel iron-catalyzed hydrosilylation of alkenes process under solvent-free conditions has been reported. The influence of the amount of Fe catalyst, reaction temperature and various alkenes and silanes on the hydrosilylation were investigated. High yields of adduct were obtained in the hydrosilylation of octene with MeCl2H, Me2ClSiH and Ph2SiH2 by using 10 mol% iron powder as a signal catalyst.

Contra-thermodynamic Olefin Isomerization by Chain-Walking Hydrofunctionalization and Formal Retro-hydrofunctionalization

We report a contra-thermodynamic isomerization of internal olefins to terminal olefins driven by redox reactions and formation of Si-F bonds. This process involves chain-walking hydrosilylation of internal olefins and subsequent formal retro-hydrosilylation. The process rests upon the high activities of platinum hydrosilylation catalysts for isomerization of metal alkyl intermediates and a new, metal-free process for the conversion of alkylsilanes to alkenes. By this approach, 1,2-disubstituted and trisubstituted olefins are converted to terminal olefins.

Platinum Catalysis Revisited-Unraveling Principles of Catalytic Olefin Hydrosilylation

Hydrosilylation of C-C multiple bonds is one of the most important applications of homogeneous catalysis in industry. The reaction is characterized by its atom-efficiency, broad substrate scope, and widespread application. To date, industry still relies on highly active platinum-based systems that were developed over half a century ago. Despite the rapid evolution of vast synthetic applications, the development of a fundamental understanding of the catalytic reaction pathway has been difficult and slow, particularly for the industrially highly relevant Karstedt's catalyst. A detailed mechanistic study unraveling several new aspects of platinum-catalyzed hydrosilylation using Karstedt's catalyst as platinum source is presented in this work. A combination of 2H-labeling experiments, 195Pt NMR studies, and an in-depth kinetic study provides the basis for a further development of the well-established Chalk-Harrod mechanism. It is concluded that the coordination strength of the olefin exerts a decisive effect on the kinetics of the reaction. In addition, it is demonstrated how distinct structural features of the active catalyst species can be derived from kinetic data. A primary kinetic isotope effect as well as a characteristic product distribution in deuterium-labeling experiments lead to the conclusion that the rate-limiting step of platinum-catalyzed hydrosilylation is in fact the insertion of the olefin into the Pt-H bond rather than reductive elimination of the product in the olefin/silane combinations studied.

Radical addition of silanes to alkenes followed by oxidation

Phenyldimethylsilane and trichlorosilane are shown to undergo efficient radical hydrosilylation reactions, on reaction with various alkenes, using triethylborane as the initiator. Adducts from the trichlorosilane reactions can be oxidised to afford alcohols in good yields. This two-step process leads to the anti-Markovnikov hydration of alkenes. Georg Thieme Verlag Stuttgart · New York.

Effect of catalysts on the reaction of allyl esters with hydrosilanes

The reaction of hydrosilylation of allyl esters XOCH 2CH=CH 2 (X = MeCO, CF 3CO, C 3F 7CO) and PhOCH 2CH=CH 2 with hydrosilanes HSiY 3 (Y = Cl, OEt) in the presence of the Speier catalyst, the Speier catalyst with additives, and of various nickel complexes was studied. The catalytic hydrosilylation reaction in the presence of the Speier catalyst is accompanied by the reduction. Additives to the Speier catalyst (vinyltriethoxysilane and some ethers) allow to suppress considerably the reduction reaction. In the presence of the studied nickel complexes mainly reduction and isomerization reactions occurred. The best nickel catalysts of hydrosilylation were the mixtures of NiCl 2 or Ni(acac) 2 with phosphine oxides. In contrast to allyl esters, the hydrosilylation of simple olefins proceeds easier, the content of the product of hydrosilylation in the reaction mixture reaches 94.3%. Pleiades Publishing, Ltd., 2010.

Novel optically active biaryl phosphorus compound and production process thereof

The invention provides a novel optically active biaryl phosphorus compound that can be produced easily without the step of optical resolution, which is almost indispensable step in a conventional method. A phosphorus compound defined by the following general formula (1): in the formula (1), R1 denotes a hydrogen atom or a hydroxy protective group; R2 denotes a group defined by the following formula (R2-1) or (R2-2); R3, R4, R5, and R6 may be the same or different and independently denote a hydrogen atom, an alkyl group, an alkoxy group, an acyloxy group, a halogen atom, a haloalkyl group, or a dialkylamino group; two among R3, R4, R5, and R6 may form an aromatic ring optionally having a substituent group, and two among R3, R4, R5, and R6 may form a methylene chain optionally having a substituent group or a (poly)methylenedioxy group optionally having a substituent group: in the formula (R2-1) and (R2-2), R7 denotes an alkyl group, a cycloalkyl group, an aryl group, an alkoxy group, or an aryloxy group; R8 and R9 independently denote a hydrogen atom, an alkyl group, or an aryl group; z denotes a divalent group; and a denotes an integer of 0 or 1.

PROCESS FOR PREPARING ORGANOCHLOROSILANES BY DEHYDROHALOGENATIVE COUPLING REACTION OF ALKYL HALIDES WITH CHLOROSILANES

The present invention relates to a process for preparing organochlorosilanes and more particularly, to the process for preparing organochlorosilanes of formula I by a dehydrohalogenative coupling of hydrochlorosilanes of formula II with organic halides of formula III in the presence of quaternary phosphonium salt as a catalyst to provide better economical matter and yield compared with conventional methods, because only catalytic amount of phosphonium chloride is required and the catalyst can be separated from the reaction mixture and recycled easily, wherein R1 represents hydrogen, chloro, or methyl; X represents chloro or bromo; R2 is selected from the group consisting of C1-17 alkyl, C1-10 fluorinated alkyl with partial or full fluorination, C2-5 alkenyl, silyl containing alkyl group represented by (CH2)nSiMe3-mClm wherein n is an integer of 0 to 2 and m is an integer of 0 to 3, aromatic group represented by Ar(R′)q wherein Ar is C6-14 aromatic hydrocarbon, R′ is C1-4 alkyl, halogen, alkoxy, or vinyl, and q is an integer of 0 to 5, haloalkyl group represented by (CH2)pX wherein p is an integer of 1 to 9 and X is chloro or bromo, and aromatic hydrocarbon represented by ArCH2X wherein Ar is C6-14 aromatic hydrocarbons and X is a chloro or bromo; R3 is hydrogen, C1-6 alkyl, aromatic group represented by Ar(R′)q wherein Ar is C6-14 aromatic hydrocarbon, R′ is C1-4 alkyl, halogen, alkoxy, or vinyl, and q is an integer of 0 to 5; and R4 in formula I is the same as R2 in formula III and further, R4 can also be (CH2)pSiR1Cl2 or ArCH2SiR1Cl2, when R2 in formula III is (CH2)pX or ArCH2X, which is formed from the coupling reaction of X—(CH2)p+1—X or XCH2ArCH2X with the compounds of formula II; or when R2 and R3 are covalently bonded to each other to form a cyclic compounds of cyclopentyl or cyclohexyl group, R3 and R4 are also covalently bonded to each other in the same fashion.