919-31-3

Basic information

• Product Name: 2-CYANOETHYLTRIETHOXYSILANE
• Synonyms: 2-Cycnoethyltriethoxysilane;B-CYANOETHYLTRIETHOXYSILANE;BETA-CYANOETHYLTRIETHOXYSILANE;3-(TRIETHOXYSILYL)PROPIONITRILE;2-CYANOETHYLTRIETHOXYSILANE;(2-cyanoethyl)triethoxy-silan;3-(triethoxysilyl)-propanenitril;3-(Triethoxysilyl)propanenitrile
• CAS NO: 919-31-3
• Molecular Formula: C₉H₁₉NO₃Si
• Molecular Weight: 217.34
• EINECS: 213-050-5
• Product Categories: Functional Materials;Si (Classes of Silicon Compounds);Silane Coupling Agents;Silane Coupling Agents (Intermediates);Si-O Compounds;Trialkoxysilanes;Chemical Synthesis;Organometallic Reagents;Organosilicon
• Mol File: 919-31-3.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 224 °C(lit.)
• Flash Point: 212 °F
• Appearance: /
• Density: 0.979 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0216mmHg at 25°C
• Refractive Index: n20/D 1.414(lit.)
• Water Solubility: Hydrolyzes in water.
• Sensitive: Moisture Sensitive
• BRN: 1776392
• CAS DataBase Reference: 2-CYANOETHYLTRIETHOXYSILANE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CYANOETHYLTRIETHOXYSILANE(919-31-3)
• EPA Substance Registry System: 2-CYANOETHYLTRIETHOXYSILANE(919-31-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 2
• RTECS: VV2750000
• F: 10-21
• TSCA: Yes
• Hazardous Substances Data: 919-31-3(Hazardous Substances Data)

Usage

Uses

(2-Cyanoethyl)triethoxysilane is an ethoxylated silicate that has been used as a coating for aluminum and quartz.

General Description

3-(Triethoxysilyl)propionitrile (TESPN) is an organosilyl sol gel that can be used as a silane based coupling agent to improve the adhesion between metal-polymeric composite. It is non-toxic and cost efficient which makes it a suitable alternative to the existing chromate treatment of metals. It can be used in surface modification of silica based surfaces.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C9H19NO3Si/c1-4-11-14(12-5-2,13-6-3)9-7-8-10/h4-7,9H2,1-3H3

Synthetic route

tetraethoxy orthosilicate (78-10-4) + acrylonitrile (107-13-1) → 2-cyanoethyltriethoxysilane (919-31-3)

Conditions	Yield
Stage #1: tetraethoxy orthosilicate at 100 - 105℃; for 2h; Molecular sieve; Large scale; Stage #2: With titanium tetrachloride In water at 40 - 98℃; Large scale; Stage #3: acrylonitrile Large scale; Further stages;	94.6%

Triethoxysilane (998-30-1) + acrylonitrile (107-13-1) → 2-cyanoethyltriethoxysilane (919-31-3)

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide at 56 - 59℃; for 2h; Large scale;	94.5%
With lithium perchlorate at 25℃; for 2h; electrolysis;	66%

ethanol (64-17-5) + 2-cyanoethyltrichlorosilane (1071-22-3) → 2-cyanoethyltriethoxysilane (919-31-3)

Conditions	Yield
In dichloromethane for 3h; Heating;	85%

P-toluenesulfonyl cyanide (19158-51-1) + C8H19IO3SiZn → 2-cyanoethyltriethoxysilane (919-31-3)

Conditions	Yield
In tetrahydrofuran at 0 - 25℃;	67%

ethanol (64-17-5) + 2-Cyanoethylsilan (18192-16-0) → 2-cyanoethyltriethoxysilane (919-31-3)

Conditions	Yield
With dihydrogen hexachloroplatinate; platinum

3-[N-(2-aminoethyl)]aminopropyltriethoxysilane (5089-72-5) → 2-cyanoethyltriethoxysilane (919-31-3)

ethanol (64-17-5) + 1,1,3,3-Tetraethoxy-1,3-bis-<2-cyan-ethyl>-disiloxan (18551-37-6) → 2-cyanoethyltriethoxysilane (919-31-3)

Conditions	Yield
With potassium hydroxide at 240℃; for 3h; Autoclave; Molecular sieve;

bis(tetrahydrofurane)dichloridodioxidomolybdenum(VI) (56907-19-8, 12081-12-8) + 2-cyanoethyltriethoxysilane (919-31-3) → MoO2Cl2NCCH2CH2Si(OC2H5)3

Conditions	Yield
In dichloromethane mixed, stirred (30 min); filtered, concd. (to dryness), washed (hexane), dried (in vac.), elem. anal.;	96%

2-cyanoethyltriethoxysilane (919-31-3) + tetrabutyl ammonium fluoride (429-41-4) → tetra-n-butylammonium octakis(2-cyanoethyl)octasilsesquioxane fluoride (1393730-72-7)

Conditions	Yield
In tetrahydrofuran; water; toluene at 25℃; for 16h; Solvent; Inert atmosphere;	96%

18-crown-6 ether (17455-13-9) + 2-cyanoethyltriethoxysilane (919-31-3) → octakis(2-cyanoethyl)octasilsesquioxane fluoride-18-crown-6-potasium

Conditions	Yield
Stage #1: 18-crown-6 ether With potassium fluoride In toluene; acetonitrile at 20℃; for 0.25h; Inert atmosphere; Stage #2: 2-cyanoethyltriethoxysilane In water; toluene; acetonitrile at 20℃; Inert atmosphere;	96%

2-cyanoethyltriethoxysilane (919-31-3) + tetraethylammonium fluoride (665-46-3) → tetraethylammonium octakis(2-cyanoethyl)octasilsesquioxane fluoride (1393730-75-0)

Conditions	Yield
In toluene at 25℃; for 16h; Solvent; Inert atmosphere;	94%

18-crown-6 ether (17455-13-9) + 2-cyanoethyltriethoxysilane (919-31-3) → octakis(2-cyanoethyl)octasilsesquioxane fluoride-18-crown-6-rubidium

Conditions	Yield
Stage #1: 18-crown-6 ether With rubidium fluoride In toluene; acetonitrile at 20℃; for 0.25h; Inert atmosphere; Stage #2: 2-cyanoethyltriethoxysilane In water; toluene; acetonitrile at 20℃; Inert atmosphere;	92%

18-crown-6 ether (17455-13-9) + 2-cyanoethyltriethoxysilane (919-31-3) + benzene-1,2-diol (120-80-9) → potassium [18-crown-6] bis(catecholato)-3-cyanoethylsilicate

Conditions	Yield
With potassium methanolate In methanol at 20℃; for 3h; Inert atmosphere;	83%

2-cyanoethyltriethoxysilane (919-31-3) → 3-aminopropyltriethoxysilane (919-30-2)

Conditions	Yield
With nickel Hydrogenation;

2-cyanoethyltriethoxysilane (919-31-3) + carbon dioxide (124-38-9) → 1,1,3,3-Tetraethoxy-1,3-bis-<2-cyan-ethyl>-disiloxan (18551-37-6) + Diethyl carbonate (105-58-8)

Conditions	Yield
With zirconium(IV) ethoxide at 180℃; under 37503.8 Torr; Autoclave;	A n/a B 48 %Chromat.

Upstream product

• 64-17-5 ethanol 
• 18551-37-6 1,1,3,3-Tetraethoxy-1,3-bis-<2-cyan-ethyl>-disiloxan 
• 78-10-4 tetraethoxy orthosilicate 
• 107-13-1 acrylonitrile 
• 5089-72-5 3-[N-(2-aminoethyl)]aminopropyltriethoxysilane 
• 19158-51-1 P-toluenesulfonyl cyanide 
• 18192-16-0 cyanoethyl silane 
• 998-30-1 Triethoxysilane 
• 1071-22-3 2-cyanoethyltrichlorosilane 

Downstream Products

• 919-30-2 3-aminopropyltriethoxysilane 
• 18551-37-6 1,1,3,3-Tetraethoxy-1,3-bis-<2-cyan-ethyl>-disiloxan 
• 105-58-8 Diethyl carbonate 

Relevant articles and documents

Sustainable Catalytic Synthesis of Diethyl Carbonate

New sustainable approaches should be developed to overcome equilibrium limitation of dialkyl carbonate synthesis from CO2 and alcohols. Using tetraethyl orthosilicate (TEOS) and CO2 with Zr catalysts, we report the first example of sustainable catalytic synthesis of diethyl carbonate (DEC). The disiloxane byproduct can be reverted to TEOS. Under the same conditions, DEC can be synthesized using a wide range of alkoxysilane substrates by investigating the effects of the number of ethoxy substituent in alkoxysilane substrates, alkyl chain, and unsaturated moiety on the fundamental property of this reaction. Mechanistic insights obtained by kinetic studies, labeling experiments, and spectroscopic investigations reveal that DEC is generated via nucleophilic ethoxylation of a CO2-inserted Zr catalyst and catalyst regeneration by TEOS. The unprecedented transformation offers a new approach toward a cleaner route for DEC synthesis using recyclable alkoxysilane.

Preparation of polyfunctional nitriles by the cyanation of functionalized organozinc halides with p-toluenesulfonyl cyanide

Various alkyl, alkenyl, akynyl, benzylic, aromatic or heterocyclic organozinc halides bearing functional groups such as an ester, a boronic ester, a cyanide, a halide or a trialkoxysilyl group react under mild conditions with p-toluenesulfonyl cyanide affording polyfunctional nitriles in 69-93% yields.

PREPARATION OF ALKOXYSILANES BY ETHERIFICATION OF CHLOROSILANES WITH REMOVAL OF HYDROGEN CHLORIDE BY VAPOR OF THE BOILING SOLVENT.

Etherification of chlorosilanes with alcohols is the usual method of obtaining alkoxysilanes. Hydrogen chloride formed as a byproduct must be removed so as to avoid side reactions and increase the yield. The vapor of boiling solvent was used as an agent to remove hydrogen chloride from the reaction zone. Various solvents were tried and their effect on yield was studied. Removal of hydrogen chloride with the vapor of the boiling solvent during etherification of chlorosilanes makes it possible to obtain alkoxysilanes in 80-90% yield as the result of strong suppression of side reactions.