5089-72-5

Usage

Chemical Properties

Colorless clear liquid

Flammability and Explosibility

Notclassified

InChI:InChI=1/C11H28N2O3Si/c1-4-14-17(15-5-2,16-6-3)11-7-9-13-10-8-12/h13H,4-12H2,1-3H3

Synthetic route

(3-chloropropyl)triethoxysilane (5089-70-3) + ethylenediamine (107-15-3) → 3-[N-(2-aminoethyl)]aminopropyltriethoxysilane (5089-72-5)

3-[N-(2-aminoethyl)]aminopropyltriethoxysilane (5089-72-5) + N-Benzyloxycarbonyl-L-proline (1148-11-4) → N,N'-bis[(S)-N-benzyloxycarbonylprolyl]-N-(2-aminoethyl-3-aminopropyl)triethoxysilylethylenediamine (502186-02-9)

Conditions	Yield
Stage #1: N-Benzyloxycarbonyl-L-proline With chloroformic acid ethyl ester; triethylamine In tetrahydrofuran at 5 - 10℃; for 0.5h; Stage #2: 3-[N-(2-aminoethyl)]aminopropyltriethoxysilane In tetrahydrofuran at 0℃; for 1h;	96%

triethanolamine (102-71-6) + 3-[N-(2-aminoethyl)]aminopropyltriethoxysilane (5089-72-5) → N-[3-(2,8,9-trioxa-5-aza-1-sila-bicyclo[3.3.3]undec-1-yl)-propyl]-ethane-1,2-diamine (52035-79-7)

Conditions	Yield
	95.4%

trimethylsilyl diethylcarbamate (18279-61-3) + 3-[N-(2-aminoethyl)]aminopropyltriethoxysilane (5089-72-5) → 2,2-dimethoxy-1,6,9,2-oxadiazasilecane (1230037-31-6)

Conditions	Yield
Inert atmosphere; Reflux;	95%

trimethylsilyl isocyanate (1118-02-1) + 3-[N-(2-aminoethyl)]aminopropyltriethoxysilane (5089-72-5) → trimethylsilyl-N'-[(E)-7,7,17,17-tetramethoxy-9-oxo-18-oxa-3,8,10,13-tetraaza-7,17-disilanonadec-1-yl]imidocarbamate (1230037-60-1)

Conditions	Yield
Reflux; Inert atmosphere;	94%

3-[N-(2-aminoethyl)]aminopropyltriethoxysilane (5089-72-5) + Methacryloyl chloride (920-46-7) → N-methacryloyl-N-(2-(N-(3-(triethoxysilyl)propyl)methacrylamido)ethyl)methacrylamide

Conditions	Yield
Stage #1: 3-[N-(2-aminoethyl)]aminopropyltriethoxysilane With trimethylamine In dichloromethane for 0.166667h; Cooling with ice; Inert atmosphere; Stage #2: Methacryloyl chloride In dichloromethane at 20℃; for 8h; Cooling with ice; Inert atmosphere;	92.8%

3-[N-(2-aminoethyl)]aminopropyltriethoxysilane (5089-72-5) + acryloyl chloride (814-68-6) → N-acryloyl-N-(2-(N-(3-(triethoxysilyl)propyl)acrylamido)ethyl)acrylamide

Conditions	Yield
Stage #1: 3-[N-(2-aminoethyl)]aminopropyltriethoxysilane With trimethylamine In dichloromethane for 0.166667h; Cooling with ice; Inert atmosphere; Stage #2: acryloyl chloride In dichloromethane at 20℃; for 8h; Cooling with ice; Inert atmosphere;	92.4%

3-[N-(2-aminoethyl)]aminopropyltriethoxysilane (5089-72-5) + N-benzyl-L-proline (31795-93-4) → N,N'-bis[(S)-N-benzylprolyl]-N-(2-aminoethyl-3-aminopropyl)triethoxysilylethylenediamine (479677-97-9)

Conditions	Yield
Stage #1: N-benzyl-L-proline With chloroformic acid ethyl ester; triethylamine In tetrahydrofuran at 5 - 10℃; for 0.5h; Stage #2: 3-[N-(2-aminoethyl)]aminopropyltriethoxysilane In tetrahydrofuran at 0℃; for 1h;	90%

3-[N-(2-aminoethyl)]aminopropyltriethoxysilane (5089-72-5) + 4-Vinylbenzyl chloride (1592-20-7) → C20H36N2O3Si

Conditions	Yield
With 2,6-di-tert-butyl-4-methyl-phenol In cyclohexane at 50 - 90℃; for 2h;	90%

3-[N-(2-aminoethyl)]aminopropyltriethoxysilane (5089-72-5) + 3-(triethoxypropyl) isocyanate (24801-88-5) → C21H49N3O7Si2

Conditions	Yield
In acetone at 65℃; for 12h;

3-[N-(2-aminoethyl)]aminopropyltriethoxysilane (5089-72-5) → N,N'-bis[(S)-prolyl]-N-(2-aminoethyl-3-aminopropyl)triethoxysilylethylenediamine (479677-96-8)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: triethylamine; ethyl chloroformate / tetrahydrofuran / 0.5 h / 5 - 10 °C 1.2: 96 percent / tetrahydrofuran / 1 h / 0 °C 2.1: 98 percent / cyclohexene / Pd/C / ethanol / 1 h / Heating View Scheme

3-[N-(2-aminoethyl)]aminopropyltriethoxysilane (5089-72-5) → N,N'-bis[(S)-N-benzylprolyl]-N-(2-aminoethyl-3-aminopropyl)triethoxysilylethylenediamine (479677-97-9)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: triethylamine; ethyl chloroformate / tetrahydrofuran / 0.5 h / 5 - 10 °C 1.2: 96 percent / tetrahydrofuran / 1 h / 0 °C 2.1: 98 percent / cyclohexene / Pd/C / ethanol / 1 h / Heating 3.1: triethylamine / tetrahydrofuran / 6 h / 0 °C View Scheme

3-[N-(2-aminoethyl)]aminopropyltriethoxysilane (5089-72-5) + 2,2-dimethyl-3-oxopropyl isobutyrate (32783-82-7) → C20H42N2O5Si

Conditions	Yield
With molecular sieves 4Å In ethanol at 28℃; for 0.25h;

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

3-[N-(2-aminoethyl)]aminopropyltriethoxysilane (5089-72-5) + calcium(II) nitrate (13477-34-4) + europium(III) nitrate → CaSiO3#dotEu(3+), β, monoclinic

Conditions	Yield
With HNO3; NH3*H2O In water solns. of Eu(NO3)3 and Ca(NO3)2 mixed (3% of Eu); pH adjusted by HNO3 and NH3*H2O to 5; stoich. amt. of Si source added; evapd.; dried (80°C, 24 h); thermolyzed (1150°C, 4 h); SEM;

lauric acid (143-07-7) + formaldehyd (50-00-0) + 3-[N-(2-aminoethyl)]aminopropyltriethoxysilane (5089-72-5) + isobutyraldehyde (78-84-2) → C28H58N2O5Si

Conditions	Yield
Stage #1: lauric acid; formaldehyd; isobutyraldehyde With toluene-4-sulfonic acid In water for 4h; Heating / reflux; Stage #2: 3-[N-(2-aminoethyl)]aminopropyltriethoxysilane In ethanol at 26℃; for 0.25h;

triethanolamine (102-71-6) + 3-[N-(2-aminoethyl)]aminopropyltriethoxysilane (5089-72-5) → N1-(3-(2,8,9-trioxa-5-aza-1-sila-bicyclo[3.3.3]undecan-1-yl)propyl)ethane-1,2-diamine (125895-13-8)

Conditions	Yield
Schlenk technique; Inert atmosphere;

(3-chloropropyl)triethoxysilane (5089-70-3) + 3-[N-(2-aminoethyl)]aminopropyltriethoxysilane (5089-72-5) → N1,N1-bis[3-(triethoxysilyl)propyl]-1,2-ethanediamine

Conditions	Yield
at 130℃; for 7h;	467.9 g

ammonium hydroxide (1336-21-6) + tetraethoxy orthosilicate (78-10-4) + 3-[N-(2-aminoethyl)]aminopropyltriethoxysilane (5089-72-5) + N-[3-(trimethoxysilyl)propyl]ethylenediamine → aminated silica

Conditions	Yield
Stage #1: ammonium hydroxide With Igepal CO-520; Igepal CO-720 In cyclohexane; water at 20℃; for 0.166667h; Stage #2: tetraethoxy orthosilicate; 3-[N-(2-aminoethyl)]aminopropyltriethoxysilane; N-[3-(trimethoxysilyl)propyl]ethylenediamine In cyclohexane; water for 12h; Stage #3: tetraethoxy orthosilicate In cyclohexane; water for 48h;

Upstream product

• 5089-70-3 (3-chloropropyl)triethoxysilane 
• 107-15-3 ethylenediamine 

Downstream Products

• 919-31-3 2-cyanoethyltriethoxysilane 
• 479677-97-9 N,N'-bis[(S)-N-benzylprolyl]-N-(2-aminoethyl-3-aminopropyl)triethoxysilylethylenediamine 
• 502186-02-9 N,N'-bis[(S)-N-benzyloxycarbonylprolyl]-N-(2-aminoethyl-3-aminopropyl)triethoxysilylethylenediamine 

Relevant academic research and scientific papers

METHOD OF PRODUCING AN AMINOALKYLALKOXYSILANE

A method of preparing an aminoalkylalkoxysilane, the method comprising reacting a haloalkylalkoxysilane with ammonia in a high pressure reactor for an amount of time sufficient to consume from 20 to 99.99 % (w/w) of the haloalkylalkoxysilane and form an aminoalkylalkoxysilane; venting ammonia from the reactor to give a mixture comprising the aminoalkylalkoxysilane, unreacted haloalkylalkoxysilane, and an ammonium halide; and treating the mixture with a primary amine to form an N-substituted aminoalkylalkoxysilane.

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The invention produces a 3-[N-(2-aminoethyl)]aminopropylalkoxysilane in high yields by reacting a 3-chloropropylalkoxysilane with ethylene diamine. A distillation pot is charged with ethylene diamine and heated above the boiling point of ethylene diamine for evaporating ethylene diamine, which is then condensed into a liquid. The liquid ethylene diamine is mixed for reaction with a 3-chloropropylalkoxysilane in such a proportion to give a molar ratio of ethylene diamine/3-chloropropylalkoxysilane of at least 12/1, thereby forming a 3-[N-(2-aminoethyl)]aminopropylalkoxysilane. The reaction solution is fed back to the pot where the unreacted ethylene diamine in the reaction solution is evaporated again and then condensed for use in a next cycle of reaction. The apparatus includes a distillation pot, a reflux condenser, a feed means and a reactor connected to form a recirculating system.

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