1067-47-6

Basic information

• Product Name: 3-CYANOPROPYLTRIETHOXYSILANE
• Synonyms: 3-CYANOPROPYLTRIETHOXYSILANE;4-(TRIETHOXYSILYL)BUTYRONITRILE;(3-cyanopropyl)triethoxy-silan;4-(triethoxysilyl)-butanenitril;4-(Triethoxysilyl)butanenitrile;4-(triethoxysilyl)-Butanenitrile;4-(triethoxysilyl)-butyronitril;Butyronitrile, 4-(triethoxysilyl)-
• CAS NO: 1067-47-6
• Molecular Formula: C₁₀H₂₁NO₃Si
• Molecular Weight: 231.36
• EINECS: 213-931-4
• Mol File: 1067-47-6.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 100-101 °C6 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 0.966 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0404mmHg at 25°C
• Refractive Index: n20/D 1.417(lit.)
• Water Solubility: Not miscible in water.
• Sensitive: Moisture Sensitive
• BRN: 1942237
• CAS DataBase Reference: 3-CYANOPROPYLTRIETHOXYSILANE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-CYANOPROPYLTRIETHOXYSILANE(1067-47-6)
• EPA Substance Registry System: 3-CYANOPROPYLTRIETHOXYSILANE(1067-47-6)

Safety Data

• Statements: 36/38
• Safety Statements: 23-24/25
• WGK Germany: 2
• RTECS: VV2785000
• F: 10-21
• TSCA: Yes
• Hazardous Substances Data: 1067-47-6(Hazardous Substances Data)

Usage

Uses

(3-Cyanopropyl)triethoxysilane is used as cyanoalkyl silane coupling agent.

General Description

3-cyanopropyltriethoxysilane (CPTS) is a trialkoxysilane with a reactive cyanoalkyl group attached to the silicon atom.

Safety Profile

Mddly toxic by ingestion. A skin irritant. When heated to decomposition it emits toxic fumes of NOx and Si.

InChI:InChI=1/C10H21NO3Si/c1-4-12-15(13-5-2,14-6-3)10-8-7-9-11/h4-8,10H2,1-3H3

Synthetic route

(3-chloropropyl)triethoxysilane (5089-70-3) → 3-cyanopropyl-triethoxysilane (1067-47-6)

Conditions	Yield
In N-methyl-acetamide	84.3%

orthoformic acid triethyl ester (122-51-0) + 4-(trichlorosilyl)butanenitrile (1071-27-8) → 3-cyanopropyl-triethoxysilane (1067-47-6)

Conditions	Yield
With aluminium trichloride for 6h; Heating;	84%

Triethoxysilane (998-30-1) + but-3-enenitrile (109-75-1) → 3-cyanopropyl-triethoxysilane (1067-47-6)

Conditions	Yield
With dihydrogen hexachloroplatinate at 80℃; for 1.5h;	45%
With dihydrogen hexachloroplatinate at 80℃; Product distribution; other reaction time;
dihydrogen hexachloroplatinate In isopropyl alcohol

hydrogen cyanide (74-90-8) + allyltriethoxysilane (2550-04-1) → 3-cyanopropyl-triethoxysilane (1067-47-6) + 2-Methyl-3-(triethylsilyl)-propionitril (27366-93-4)

Conditions	Yield
Pd catalyst

ethanol (64-17-5) + 4-(trichlorosilyl)butanenitrile (1071-27-8) → 3-cyanopropyl-triethoxysilane (1067-47-6)

18-crown-6 ether (17455-13-9) + 3-cyanopropyl-triethoxysilane (1067-47-6) → octakis(3-cyanopropyl)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: 3-cyanopropyl-triethoxysilane In water; toluene; acetonitrile at 20℃; Inert atmosphere;	87%

3-cyanopropyl-triethoxysilane (1067-47-6) + tetrabutyl ammonium fluoride (429-41-4) → tetra-n-butylammonium octakis(3-cyanopropyl)octasilsesquioxane fluoride (1393730-73-8)

Conditions	Yield
In tetrahydrofuran; water; toluene at 25℃; for 16h; Solvent; Inert atmosphere;	86%

3-cyanopropyl-triethoxysilane (1067-47-6) → (4-aminobutyl)-triethoxysilane (3069-30-5)

Conditions	Yield
With hydrogen; Raney-Co In diethyl ether at 85 - 95℃; under 76000 Torr;
With hydrogen; carbon monoxide In ethanol

polymer, EO20PO70EO20 (EO = ethylene oxide, PO = propylene oxide), MA 5800 Da; monomer(s): ethylene oxide; propylene oxide + 3-cyanopropyl-triethoxysilane (1067-47-6) → polymer; monomer(s): ethylene oxide; propylene oxide; tetraethoxysilane

Conditions	Yield
With hydrogenchloride In water at 35℃; for 20h;

polymer; monomer(s): ethylene oxide; propylene oxide; tetraethoxysilane + 3-cyanopropyl-triethoxysilane (1067-47-6) → polymer; monomer(s): ethylene oxide; propylene oxide; tetraethoxysilane; 3-cyanopropyltriethoxysilane

Conditions	Yield
In toluene for 18h; Heating;

3-cyanopropyl-triethoxysilane (1067-47-6) + cadmium(II) acetate dihydrate (5743-04-4) + ethanolamine (141-43-5) → 2-[3-(triethoxysilyl)propyl]-1,3-oxazoline (195528-18-8)

3-cyanopropyl-triethoxysilane (1067-47-6) → 4-(triethoxysilyl)butanoic acid (68896-01-5)

Conditions	Yield
With sulfuric acid In water at 59.84 - 92.84℃; for 24h;

diammonium closo-decahydrodecaborate + 3-cyanopropyl-triethoxysilane (1067-47-6) → [NH4][2-B10H9NC(CH2)3Si(OC2H5)3] + 2,6-B10H8[NC(CH2)3Si(OC2H5)3]2

Conditions	Yield
at 140℃; for 48h; Inert atmosphere; Schlenk technique;

3-cyanopropyl-triethoxysilane (1067-47-6) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → C22H47B2NO7Si

Conditions	Yield
With [(Me3Si)2N]2Th[κ2-(N,C)-CH2Si(CH3)2N(SiMe3)] In benzene-d6 at 80℃; for 8h; Catalytic behavior; Sealed tube;	95 %Spectr.

Upstream product

• 998-30-1 Triethoxysilane 
• 109-75-1 but-3-enenitrile 
• 5089-70-3 (3-chloropropyl)triethoxysilane 
• 64-17-5 ethanol 
• 1071-27-8 4-(trichlorosilyl)butanenitrile 
• 74-90-8 hydrogen cyanide 
• 2550-04-1 allyltriethoxysilane 
• 122-51-0 orthoformic acid triethyl ester 

Downstream Products

• 3069-30-5 (4-aminobutyl)-triethoxysilane 

Relevant articles and documents

Reaction of the Si-Cl bond with trialkyl orthoformates preparation of alkoxy-substituted silanes

Trialkyl orthoformates in the presence of aluminium chloride represent quite useful reagents to generate silicon alkoxides from chlorosilanes. 3-Cyanopropyltrichlorosilane and 2-[(2-trichlorosilyl)ethyl]-pyridine give the triethoxy compounds 3-cyanopropyltriethoxysilane and 2-[(2-triethoxysilyl)ethyl]-pyridine respectively. Via this route, in methylchlorooligosilanes a partial or complete exchange of the chlorine substituents for alkoxy groups occurs depending on the starting molar ratio of silane:HC(OR)3 (R = Me, Et). SiCl2Me groups react to SiClMe(OR) first before SiMe(OR)2 groups are formed. (Si)2SiClMe units are not affected by HC(OR)3.

Method and apparatus for the preparation of cyanoalkyl-alkoxysilanes

In a method of preparing cyanoalkyl-akoxysilanes, which is suitable for the production of these silanes on a large technical scale, the reaction of a chloroalkyl-alkoxysilane with an alkali metal cyanide in the presence of a solvent takes place in a stirring reactor which is provided with means for loading these starting materials and with an outlet opening for the alkali metal chloride by-product, and which is connected through a bypass valve to a column with a superimposed condenser. After the reaction in the reactor has ended, first the solvent is distilled out through the column and then the main part of the cyanosilane, and then the rest of the cyanosilane is distilled out while bypassing the column. The alkali metal chloride is then removed from the reactor through a lock.