13497-18-2

Basic information

• Product Name: Bis[3-(triethoxysilyl)propyl]amine
• Synonyms: 3-(triethoxysilyl)-N-[3-(triethoxysilyl)propyl]-1-Propanamine;BIS(TRIETHOXYSILYLPROPYL)AMINE;BIS[3-(TRIETHOXYSILYL)PROPYL]AMINE;Bis-[3-(Triethoxysilyl)propyl];Iminobis(3,1-propanediyl)bis(triethoxysilane);Iminobis(trimethylene)bis(triethoxysilane);N,N-Bis(3-triethoxysilylpropyl)amine;Bis(3-(triethoxysilyl)
• CAS NO: 13497-18-2
• Molecular Formula: C₁₈H₄₃NO₆Si₂
• Molecular Weight: 425.71
• EINECS: 236-818-1
• Product Categories: Industrial/Fine Chemicals;Amino Silanes
• Mol File: 13497-18-2.mol
• Article Data: 8

Chemical Properties

• Melting Point: <0°C
• Boiling Point: 160 °C
• Flash Point: 162°C
• Appearance: Yellowish clear liquid
• Density: 0.973
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.429
• Storage Temp.: 2-8°C(protect from light)
• PKA: 10.54±0.19(Predicted)
• Water Solubility: 23-1000000mg/L at 20℃
• CAS DataBase Reference: Bis[3-(triethoxysilyl)propyl]amine(CAS DataBase Reference)
• NIST Chemistry Reference: Bis[3-(triethoxysilyl)propyl]amine(13497-18-2)
• EPA Substance Registry System: Bis[3-(triethoxysilyl)propyl]amine(13497-18-2)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-28-36/37/39-45-24/25
• RIDADR: 2735
• TSCA: Yes
• Hazardous Substances Data: 13497-18-2(Hazardous Substances Data)

Usage

Chemical Properties

Yellowish clear liquid

Flammability and Explosibility

Notclassified

InChI:InChI=1/C18H43NO6Si2/c1-9-17(26(20-11-3,21-12-4)22-13-5)19-18(10-2)27(23-14-6,24-15-7)25-16-8/h17-19H,9-16H2,1-8H3

Synthetic route

(3-chloropropyl)triethoxysilane (5089-70-3) → bis-(3-triethoxysilylpropyl)amine (13497-18-2) + tris-<3-triethoxysilanyl-propyl>-amine and 3-triethoxysilanyl-propylamine

Conditions	Yield
With ammonia

3-aminopropyltriethoxysilane (919-30-2) + (3-chloropropyl)triethoxysilane (5089-70-3) → bis-(3-triethoxysilylpropyl)amine (13497-18-2)

Conditions	Yield
at 70℃; for 5.5h; Inert atmosphere;	482 g

bis-(3-triethoxysilylpropyl)amine (13497-18-2) + 1,3-chlorobromopropane (109-70-6) → 3-chloro-N,N-bis(3-(triethoxysilyl)propyl)propane-1-amine

Conditions	Yield
With calcium hydride In N,N-dimethyl-formamide at 23℃; for 15h; Reagent/catalyst;	99%
With calcium hydride In N,N-dimethyl-formamide at 23℃; for 15h;	99%

2-methoxyethyl acrylate (3121-61-7) + bis-(3-triethoxysilylpropyl)amine (13497-18-2) → 2-methoxyethyl 3-(bis(3-triethoxysilylpropyl)amino)propanoate

Conditions	Yield
In ethanol at 20℃; for 8h; Inert atmosphere;	97.3%

Thiobutyrolactone (1003-10-7) + bis-(3-triethoxysilylpropyl)amine (13497-18-2) → 4-mercapto-N,N-bis(3-(triethoxysilyl)propyl)butanamide (1333386-63-2)

Conditions	Yield
In toluene for 48h; Reflux; Inert atmosphere;	96%

formaldehyd (50-00-0) + ethanol (64-17-5) + bis-(3-triethoxysilylpropyl)amine (13497-18-2) → N-(ethoxymethyl)-N,N-bis(3-triethoxysilylpropyl)amine (1440531-01-0)

Conditions	Yield
at 80℃; for 0.0833333h; Inert atmosphere;	95%
at 80℃; for 0.0833333h; Inert atmosphere;	95 mg

bis-(3-triethoxysilylpropyl)amine (13497-18-2) + propargyl bromide (106-96-7) → N,N-bis((3-triethoxysilyl)propyl)prop-2-yn-1-amine

Conditions	Yield
With calcium hydride In tetrahydrofuran; water; toluene at 20℃; Inert atmosphere; Schlenk technique;	95%
In tetrahydrofuran; water; toluene at 20℃;	95%
With calcium hydride In tetrahydrofuran; water; toluene at 20℃; for 16h;	95%

1-azido-2-iodoethane (42059-30-3) + bis-(3-triethoxysilylpropyl)amine (13497-18-2) → N‐(2‐azidoethyl)‐3‐(triethoxysilyl)‐N‐(3‐(triethoxysilyl)propyl)propan‐1‐amine

Conditions	Yield
With potassium carbonate In acetonitrile at 85℃; for 16h; Inert atmosphere; Schlenk technique; Sealed tube;	95%
With potassium carbonate In acetonitrile at 85℃; for 18h; Sealed tube; Inert atmosphere;

bis-(3-triethoxysilylpropyl)amine (13497-18-2) + 3-(trimethylsilyl)prop-2-yn-1-yl 4-methylbenzenesulfonate (71321-16-9) → (3-trimethylsilylprop-2-ynyl)bis(3-triethoxysilylpropyl)amine

Conditions	Yield
With potassium carbonate In acetonitrile at 85℃; for 15h;	94%

bis-(3-triethoxysilylpropyl)amine (13497-18-2) + phenoxy tetraethyleneglycol acrylate → 2-(2-(2-(2-phenoxyethoxy)ethoxy)ethoxy)ethyl 3-(bis(3-(triethoxysilyl)propyl)amino)propanoate

Conditions	Yield
In ethanol at 20℃; for 8h; Inert atmosphere;	93.7%

bis-(3-triethoxysilylpropyl)amine (13497-18-2) + methoxy PEG(350) monoacrylate → 2,5,8,11,14,17,20,23,26-nonaoxaoctacosan-28-yl 3-(bis(3-(triethoxysilyl)propyl)amino)propanoate

Conditions	Yield
In ethanol at 20℃; for 8h; Inert atmosphere;	93.5%

bis-(3-triethoxysilylpropyl)amine (13497-18-2) + 1-azido-3-iodopropane (58503-62-1) → 3‐azido‐N,N‐bis(3‐(triethoxysilyl)propyl)propan‐1‐amine

Conditions	Yield
With potassium carbonate In acetonitrile at 85℃; for 16h; Inert atmosphere; Schlenk technique; Sealed tube;	93%
With potassium carbonate In acetonitrile at 85℃; for 16h; Sealed tube; Inert atmosphere;	93%

2-(dimethylamino)ethyl methacrylate (2439-35-2) + bis-(3-triethoxysilylpropyl)amine (13497-18-2) → 2-(dimethylamino)ethyl 3-(bis(3-triethoxysilylpropyl)amino)propanoate

Conditions	Yield
In ethanol at 20℃; for 8h; Inert atmosphere;	91.7%

bis-(3-triethoxysilylpropyl)amine (13497-18-2) + 2-phenoxyethyl acrylate (48145-04-6) → 2-phenoxyethyl 3-(bis(3-(triethoxysilyl)propyl)amino)propanoate

Conditions	Yield
In ethanol at 20℃; for 8h; Inert atmosphere;	91.6%

bis-(3-triethoxysilylpropyl)amine (13497-18-2) + C16H18ClNO4 → C34H60N2O10Si2*ClH

Conditions	Yield
In dichloromethane at 25℃; for 60h; Inert atmosphere;	81%

bis-(3-triethoxysilylpropyl)amine (13497-18-2) + 1-(3-bromopropyl)-1H-imidazole (144385-79-5) → N-(3-(1H-imidazole-1-yl)propyl)-3-(triethoxysilyl)-N-(3-(triethoxysilyl)propyl)propane-1-amine

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 60℃; for 16h;	65%

bis-(3-triethoxysilylpropyl)amine (13497-18-2) + 3-(triethoxypropyl) isocyanate (24801-88-5) → N,N,N'-tris-(3-triethoxysilylpropyl)urea

Conditions	Yield
In methanol for 19h;

bis-(3-triethoxysilylpropyl)amine (13497-18-2) + oxiranyl-methanol (556-52-5) → C27H55N3O10Si2

Conditions	Yield
Stage #1: bis-(3-triethoxysilylpropyl)amine; isophorone diisocyanate In butanone at 10 - 20℃; Stage #2: oxiranyl-methanol In butanone at 20 - 60℃; for 24h;

bis-(3-triethoxysilylpropyl)amine (13497-18-2) → 3-(triethoxysilyl)-N,N-bis[3-(triethoxysilyl)propyl]-1-propanamine (18784-74-2)

Conditions	Yield
With hydrogen; palladium on activated charcoal at 195℃; for 12.6667h; Product distribution / selectivity; Inert atmosphere;

bis-(3-triethoxysilylpropyl)amine (13497-18-2) → C27H58N4O6Si2

Conditions	Yield
Multi-step reaction with 2 steps 1: calcium hydride / tetrahydrofuran; water; toluene / 20 °C / Inert atmosphere; Schlenk technique 2: bromotris(triphenylphosphine)copper(I); triethylamine / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere; Sealed tube View Scheme
Multi-step reaction with 2 steps 1: tetrahydrofuran; toluene; water / 20 °C 2: triethylamine; [CuBr(PPh3)3] / tetrahydrofuran / 48 h / 20 °C / Inert atmosphere; Schlenk technique View Scheme

bis-(3-triethoxysilylpropyl)amine (13497-18-2) → C28H52N4O6Si2

Conditions	Yield
Multi-step reaction with 2 steps 1: calcium hydride / tetrahydrofuran; water; toluene / 20 °C / Inert atmosphere; Schlenk technique 2: bromotris(triphenylphosphine)copper(I); triethylamine / tetrahydrofuran / 0.08 h / 100 °C / Inert atmosphere; Sealed tube; Microwave irradiation View Scheme

bis-(3-triethoxysilylpropyl)amine (13497-18-2) → C32H68N4O7Si2

Conditions	Yield
Multi-step reaction with 2 steps 1: calcium hydride / tetrahydrofuran; water; toluene / 20 °C / Inert atmosphere; Schlenk technique 2: bromotris(triphenylphosphine)copper(I); triethylamine / tetrahydrofuran / 0.33 h / 100 °C / Inert atmosphere; Sealed tube; Microwave irradiation View Scheme

bis-(3-triethoxysilylpropyl)amine (13497-18-2) → C25H52N4O8Si2

Conditions	Yield
Multi-step reaction with 2 steps 1: calcium hydride / tetrahydrofuran; water; toluene / 20 °C / Inert atmosphere; Schlenk technique 2: bromotris(triphenylphosphine)copper(I); triethylamine / tetrahydrofuran / 0.08 h / 100 °C / Inert atmosphere; Sealed tube; Microwave irradiation View Scheme

bis-(3-triethoxysilylpropyl)amine (13497-18-2) → C27H59N4O9PSi2

Conditions	Yield
Multi-step reaction with 2 steps 1: calcium hydride / tetrahydrofuran; water; toluene / 20 °C / Inert atmosphere; Schlenk technique 2: bromotris(triphenylphosphine)copper(I); triethylamine / tetrahydrofuran / 0.17 h / 100 °C / Inert atmosphere; Sealed tube; Microwave irradiation View Scheme

bis-(3-triethoxysilylpropyl)amine (13497-18-2) → C30H66N4O9Si3

Conditions	Yield
Multi-step reaction with 2 steps 1: calcium hydride / tetrahydrofuran; water; toluene / 20 °C / Inert atmosphere; Schlenk technique 2: bromotris(triphenylphosphine)copper(I); triethylamine / tetrahydrofuran / 0.33 h / 100 °C / Inert atmosphere; Sealed tube; Microwave irradiation View Scheme

bis-(3-triethoxysilylpropyl)amine (13497-18-2) → C29H55N9O6Si2

Conditions	Yield
Multi-step reaction with 2 steps 1: calcium hydride / tetrahydrofuran; water; toluene / 20 °C / Inert atmosphere; Schlenk technique 2: bromotris(triphenylphosphine)copper(I); triethylamine / tetrahydrofuran / 0.17 h / 100 °C / Inert atmosphere; Sealed tube; Microwave irradiation View Scheme

bis-(3-triethoxysilylpropyl)amine (13497-18-2) → C52H110N8O12Si4

Conditions	Yield
Multi-step reaction with 2 steps 1: calcium hydride / tetrahydrofuran; water; toluene / 20 °C / Inert atmosphere; Schlenk technique 2: bromotris(triphenylphosphine)copper(I); triethylamine / tetrahydrofuran / 0.33 h / 100 °C / Inert atmosphere; Sealed tube; Microwave irradiation View Scheme

bis-(3-triethoxysilylpropyl)amine (13497-18-2) → C50H98N8O12Si4

Conditions	Yield
Multi-step reaction with 2 steps 1: calcium hydride / tetrahydrofuran; water; toluene / 20 °C / Inert atmosphere; Schlenk technique 2: bromotris(triphenylphosphine)copper(I); triethylamine / tetrahydrofuran / 0.17 h / 100 °C / Inert atmosphere; Sealed tube; Microwave irradiation View Scheme

bis-(3-triethoxysilylpropyl)amine (13497-18-2) → C26H54N4O8Si2

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / acetonitrile / 16 h / 85 °C / Inert atmosphere; Schlenk technique; Sealed tube 2: bromotris(triphenylphosphine)copper(I); triethylamine / tetrahydrofuran / 0.08 h / 100 °C / Inert atmosphere; Sealed tube; Microwave irradiation View Scheme

bis-(3-triethoxysilylpropyl)amine (13497-18-2) → C29H55N9O6Si2

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / acetonitrile / 16 h / 85 °C / Inert atmosphere; Schlenk technique; Sealed tube 2: bromotris(triphenylphosphine)copper(I); triethylamine / N,N-dimethyl-formamide / 0.08 h / 100 °C / Inert atmosphere; Sealed tube; Microwave irradiation View Scheme

Upstream product

• 919-30-2 3-aminopropyltriethoxysilane 
• 5089-70-3 (3-chloropropyl)triethoxysilane 

Relevant articles and documents

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