1760-24-3

Basic information

• Product Name: N-[3-(Trimethoxysilyl)propyl]ethylenediamine
• Synonyms: 3-(2-Aminoethylamino)propyltrimethoxysilane N-(2-Aminoethyl)-3-aminopropyltrimethoxysilane N-(3-Trimethoxysilylpro;N-(2-Aminoethyl)-3-aminopropyltrimethoxysilane for synthesis;N-BETA-(AMINOETHYL)-GAMMA-AMINOPROPYLTRIMETHOXYSILANE;N-(2-AMINOETHYL)-3-AMINOPROPYLTRIMETHOXYSILANE;N-(2-AMINOETHYL)-3-(TRIMETHOXYSILYL)PROPYLAMINE;N-[3-(TRIMETHOXYSILYL)PROPYL]ETHYLENEDIAMINE;(3-(2-aminoethyl)aminopropyl)trimethoxy-silan;(aminoethyl)-aminopropyltrimethoxysilane
• CAS NO: 1760-24-3
• Molecular Formula: C₈H₂₂N₂O₃Si
• Molecular Weight: 222.36
• EINECS: 217-164-6
• Product Categories: silane;Halogenated Heterocycles ,Others ,Oxadiazoles;Amino;Amino Silanes (Silane Coupling Agents);Functional Materials;Si (Classes of Silicon Compounds);Silane Coupling Agents;Si-O Compounds;Trialkoxysilanes;Adhesion Promoters;Amino Silanes;Coupling Agents;Dispersing Agents;Surface Modifiers;Silane series
• Mol File: 1760-24-3.mol

Chemical Properties

• Melting Point: 0°C
• Boiling Point: 146 °C15 mm Hg(lit.)
• Flash Point: 220 °F
• Appearance: Clear colorless to light yellow/Liquid
• Density: 1.028 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.059mmHg at 25°C
• Refractive Index: n20/D 1.444(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: Miscible with toluene.
• PKA: 10.11±0.19(Predicted)
• Water Solubility: REACTS
• Sensitive: Air & Moisture Sensitive
• BRN: 636230
• CAS DataBase Reference: N-[3-(Trimethoxysilyl)propyl]ethylenediamine(CAS DataBase Reference)
• NIST Chemistry Reference: N-[3-(Trimethoxysilyl)propyl]ethylenediamine(1760-24-3)
• EPA Substance Registry System: N-[3-(Trimethoxysilyl)propyl]ethylenediamine(1760-24-3)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 38-41-43-52/53-42/43-37/38
• Safety Statements: 26-39-61-37/39-24-36/37/39-23
• RIDADR: UN 3267 8/PG 2
• WGK Germany: 3
• RTECS: KV7400000
• F: 1-10
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 1760-24-3(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 1760-24-3 differently. You can refer to the following data:
1. This substance is used in the following products: adhesives and sealants, coating products and finger paints. Other release to the environment of this substance is likely to occur from: indoor use and outdoor use resulting in inclusion into or onto a materials (e.g. binding agent in paints and coatings or adhesives).
2. N-[3-(Trimethoxysilyl)propyl]ethylenediamine has also been used as an organic ligand for the surface modification of silica gel to uptake heavy metal ions. It can react with fluorinated carbon nanotubes (F-CNT) to form aminoalkylalkoxysilane functionalized carbon nanotubes.
3. [3-(2-Aminoethylamino)propyl]trimethoxysilane has been used in the synthesis of various polyhedral silsesquioxanes, (RSiO1.5)n (SSQO).It can be functionalized onto the mesoporous SBA-15 silica to be used as matrices for controlled drug delivery.It is also used in the synthesis of silane-based polymer, which is used in conducting instant adhesives.

service life

Other release to the environment of this substance is likely to occur from: outdoor use in long-life materials with low release rate (e.g. metal, wooden and plastic construction and building materials) and indoor use in long-life materials with low release rate (e.g. flooring, furniture, toys, construction materials, curtains, foot-wear, leather products, paper and cardboard products, electronic equipment).

Introduction

N-[3-(Trimethoxysilyl)propyl]ethylenediamine (equal to A-1120, GF 91, KBM603) is a clear, colorless, strongly alkaline liquid with smell being very sensitive to hydrolysis. The chloride content ranges in the lower ppm-level. N-[3-(Trimethoxysilyl)propyl]ethylenediamine is used as adhesion promoter at organic/inorganic interfaces, for modification of surfaces (corrosion prevention, component of primers) or silicone-polymers or as crosslinker (moisture crosslinking of polymers). The application as "coupling agent" leads in general to an improvement of mechanical and electrical product properties above all under exposure to heat and/or moisture. Applications: N-[3-(Trimethoxysilyl)propyl]ethylenediamine may be used as an effective coupling agent for clay reinforced elastomers such as natural and nitrile rubber, to improve physical and dynamic properties. Used as an effective coupling agent for mineral reinforced nylon 6, nylon 6/6 and polybutyleneterephthalate, to increase the flexural and tensile strength of the thermoplastic composite. Used as a fiberglass finish or a resinous additive for fiberglass reinforced phenolic, melamine and expoxy thermoset composites. Used as a mineral binders in in foundry and abrasive composite applications, to improve adhesion, increase composite strength. Used as a glass and metal primer, to improve the adhesion of many coatings (urethanes, epoxies, phenolics and others) to glass and metal surfaces. Used as an adhesion promoters in polysulfide, polyvinyl chloride plastisol, silicone two part urethane and epoxy adhesives and sealants.

Chemical Properties

Colorless transparent liquid

Flammability and Explosibility

Notclassified

Contact allergens

This amine-functional methoxysilane, referenced as aminoethyl aminopropyltrimethoxysilane, was impli- cated in the production of glass filaments.

InChI:InChI=1/C8H22N2O3Si/c1-5-8(10-7-6-9)14(11-2,12-3)13-4/h8,10H,5-7,9H2,1-4H3

Synthetic route

ethylenediamine (107-15-3) + 3-Chloropropyltrimethoxysilan (2530-87-2) → [1-(2-aminoethyl)-3-aminopropyl]trimethoxysilane (1760-24-3)

Conditions	Yield
Heating;	90%

3-Chloropropyltrimethoxysilan (2530-87-2) → [1-(2-aminoethyl)-3-aminopropyl]trimethoxysilane (1760-24-3)

Conditions	Yield
In ethylenediamine	70.1%

methanol (67-56-1) + C11H28N2O4Si → 2-ethoxy-ethanol (110-80-5) + [1-(2-aminoethyl)-3-aminopropyl]trimethoxysilane (1760-24-3)

Conditions	Yield
at 20℃; Kinetics; Equilibrium constant; Further Variations:; Temperatures;

phenyl isothiocyanate (103-72-0) + [1-(2-aminoethyl)-3-aminopropyl]trimethoxysilane (1760-24-3) → C22H32N4O3S2Si

Conditions	Yield
In ethanol for 0.25h; Heating;	100%

1-[(2-oxazepan-1-yl)carbonyl]azepan-2-one (19494-73-6) + [1-(2-aminoethyl)-3-aminopropyl]trimethoxysilane (1760-24-3) → caprolactam (105-60-2) + C15H31N3O5Si

Conditions	Yield
In toluene at 75℃; for 3h;	A n/a B 100%

2-Isocyanatoethyl methacrylate (30674-80-7) + [1-(2-aminoethyl)-3-aminopropyl]trimethoxysilane (1760-24-3) → 4,9-dioxo-5-(3-(trimethoxysilyl)propyl)-3,5,8,10-tetraazadodecane-1,12-diyl bis(2-methylacrylate)

Conditions	Yield
at 55℃;	100%

carbon disulfide (75-15-0) + [1-(2-aminoethyl)-3-aminopropyl]trimethoxysilane (1760-24-3) → C10H20N2O3S4Si(2-)*2Li(1+)

Conditions	Yield
With lithium hydride In tetrahydrofuran for 2h; Heating;	99%

N,N-Dimethylacrylamide (2680-03-7) + [1-(2-aminoethyl)-3-aminopropyl]trimethoxysilane (1760-24-3) → C13H31N3O4Si

Conditions	Yield
at 70 - 100℃; for 8.5h;	98%

N,N-dimethyl-formamide dimethyl acetal (4637-24-5) + [1-(2-aminoethyl)-3-aminopropyl]trimethoxysilane (1760-24-3) → 1-[3-(trimethoxysilyl)propyl]-4,5-dihydro-1H-imidazole

Conditions	Yield
In toluene at 80℃; for 24h;	98%

maleic anhydride (108-31-6) + 3-methyl-Δ4-tetrahydrophthalic anhydride (5333-84-6) + [1-(2-aminoethyl)-3-aminopropyl]trimethoxysilane (1760-24-3) → C17H32N2O6Si

Conditions	Yield
In ethyl acetate at 50 - 60℃;	97%

maleic anhydride (108-31-6) + [1-(2-aminoethyl)-3-aminopropyl]trimethoxysilane (1760-24-3) → (E)3-{N-[3-(trimethoxysilyl)propylammonioethyl]carbamoyl}propenoate

Conditions	Yield
In ethyl acetate at 50 - 60℃;	97%

phthalic anhydride (85-44-9) + [1-(2-aminoethyl)-3-aminopropyl]trimethoxysilane (1760-24-3) → C16H26N2O6Si

Conditions	Yield
In ethyl acetate at 50 - 60℃;	97%

carbon disulfide (75-15-0) + [1-(2-aminoethyl)-3-aminopropyl]trimethoxysilane (1760-24-3) → C10H20N2O3S4Si(2-)*2Na(1+)

Conditions	Yield
With sodium hydride In tetrahydrofuran for 2h; Heating;	96%

Trimethylsilanol (1066-40-6) + [1-(2-aminoethyl)-3-aminopropyl]trimethoxysilane (1760-24-3) → 1-[3-N-(2-aminoethyl)aminopropyl]-1,1-dimethoxy-3,3,3-trimethyldisiloxane (199327-09-8)

Conditions	Yield
at 20℃;	95.5%

carbon disulfide (75-15-0) + [1-(2-aminoethyl)-3-aminopropyl]trimethoxysilane (1760-24-3) → C10H20N2O3S4Si(2-)*2K(1+)

Conditions	Yield
With potassium hydride In tetrahydrofuran for 2h; Heating;	95%

{Bu2Sn(diethylmalonato)}x + [1-(2-aminoethyl)-3-aminopropyl]trimethoxysilane (1760-24-3) → {Bu2Sn(diethylmalonato)(γ-((aminoethyl)amino)propyl)trimethoxysilane}x

Conditions	Yield
In dichloromethane dissolved together in dry CH2Cl2; evapn. in vac., oil crystd. after standing at 25°C for several days, recrystn. from CH2Cl2 at -30°C; elem. anal.;	95%

toluene diisocyanate trimer (98474-79-4) + [1-(2-aminoethyl)-3-aminopropyl]trimethoxysilane (1760-24-3) → C35H40N8O9Si

Conditions	Yield
With dibutyltin dilaurate In tetrahydrofuran at 20℃; for 5h; Dry environment;	95%

1-(2-chlorovinyl)benzene (622-25-3) + acetic acid (64-19-7) + [1-(2-aminoethyl)-3-aminopropyl]trimethoxysilane (1760-24-3) → N'-aminoethyl-N-vinylbenzyl-N-aminopropylpolysiloxane hydroacetate

Conditions	Yield
Stage #1: [1-(2-aminoethyl)-3-aminopropyl]trimethoxysilane With water In methanol for 1h; Stage #2: 1-(2-chlorovinyl)benzene at 50 - 64℃; for 3h; Stage #3: acetic acid With 2,6-di-tert-butyl-4-methyl-phenol; sodium methylate more than 3 stages;	94%
Stage #1: [1-(2-aminoethyl)-3-aminopropyl]trimethoxysilane With water In methanol for 1h; Stage #2: 1-(2-chlorovinyl)benzene at 50 - 64℃; for 3h; Stage #3: acetic acid With 4-tert-Butylcatechol; sodium methylate more than 3 stages;	88%

Trimethylsilanol (1066-40-6) + [1-(2-aminoethyl)-3-aminopropyl]trimethoxysilane (1760-24-3) → 3-[3-N-(2-aminoethyl)aminopropyl]-3-methoxy-1,1,1,5,5,5-hexamethyltrisiloxane

Conditions	Yield
Heating;	92.5%

[1-(2-aminoethyl)-3-aminopropyl]trimethoxysilane (1760-24-3) + n-hexadecanoyl chloride (112-67-4) → [2-(N-hexadecanoylamino)ethyl]-[3-(trimethoxysilyl)propyl]ammonium chloride

Conditions	Yield
In dichloromethane Cooling with ice;	92%

bis(2-hydroxyethyl)(2-hydroxybutyl)amine (4435-57-8) + [1-(2-aminoethyl)-3-aminopropyl]trimethoxysilane (1760-24-3) → 1[N-(2-aminoethyl)aminopropyl]-3-ethylsilatrane

Conditions	Yield
With potassium hydroxide In toluene for 3h; Heating;	91.8%

acryloyl chloride (814-68-6) + [1-(2-aminoethyl)-3-aminopropyl]trimethoxysilane (1760-24-3) → N-acryloyl-N-(2-(N-(3-(trimethoxysilyl)propyl)acrylamido)ethyl)acrylamide

Conditions	Yield
Stage #1: [1-(2-aminoethyl)-3-aminopropyl]trimethoxysilane 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;	91.8%

ethanolamine (141-43-5) + [1-(2-aminoethyl)-3-aminopropyl]trimethoxysilane (1760-24-3) → C11H31N5O3Si (1134640-03-1)

Conditions	Yield
Heating;	91.3%

di-μ-chloro-bis(1,5-cyclooctadiene)dirhodium (12092-47-6) + [1-(2-aminoethyl)-3-aminopropyl]trimethoxysilane (1760-24-3) → Rh(C8H12)(1+)*NH2(CH2)2NH(CH2)3Si(OCH3)3*Cl(1-)=Rh(C8H12)[NH2(CH2)2NH(CH2)3Si(OCH3)3]Cl (255390-98-8, 237428-36-3)

Conditions	Yield
In dichloromethane (N2); stirring (room temp., 1 h); washing (hexane), dryig (vac.); elem. anal.;	91%

n-dodecanoyl chloride (112-16-3) + [1-(2-aminoethyl)-3-aminopropyl]trimethoxysilane (1760-24-3) → [2-(N-dodecanoylamino)ethyl]-[3-(trimethoxysilyl)propyl]ammonium chloride

Conditions	Yield
In dichloromethane Cooling with ice;	90%

2-hydroxy-5-methoxybenzaldehyde (672-13-9) + [1-(2-aminoethyl)-3-aminopropyl]trimethoxysilane (1760-24-3) → N-[N-(3-(trimethoxysilyl)propyl)ethylenediamine]-5-methoxysalicylaldimine (1293408-57-7)

Conditions	Yield
With formic acid In ethanol for 6h; Reflux;	88%

4-(pyrrolidin-1-yl)benzaldehyde (51980-54-2) + [1-(2-aminoethyl)-3-aminopropyl]trimethoxysilane (1760-24-3) → ((4-pyrrolidin-1-yl)benzylidene)-3-(trimethoxysilyl)propylethane-1,2-diamine

Conditions	Yield
In toluene for 4h; Inert atmosphere; Reflux;	87%

2-methoxy-3-methylbenzaldehyde (824-42-0) + [1-(2-aminoethyl)-3-aminopropyl]trimethoxysilane (1760-24-3) → N-[N-(3-(trimethoxysilyl)propyl)ethylenediamine]-3-methylsalicylaldimine (1293408-54-4)

Conditions	Yield
With formic acid In ethanol for 6h; Reflux;	85%

ruthenium(II) bis(triphenylphosphine) dichloride + dichloromethane (75-09-2) + [1-(2-aminoethyl)-3-aminopropyl]trimethoxysilane (1760-24-3) → C44H52Cl2N2O3P2RuSi*CH2Cl2

Conditions	Yield
Stage #1: ruthenium(II) bis(triphenylphosphine) dichloride; [1-(2-aminoethyl)-3-aminopropyl]trimethoxysilane In tetrahydrofuran for 4h; Reflux; Inert atmosphere; Schlenk technique; Stage #2: dichloromethane In hexane	85%

4-(4-morpholinyl)benzaldehyde (1204-86-0) + [1-(2-aminoethyl)-3-aminopropyl]trimethoxysilane (1760-24-3) → (4-morpholinobenzylidene)-3-(trimethoxysilyl)propylethane-1,2-diamine

Conditions	Yield
In toluene for 4h; Inert atmosphere; Reflux;	85%

4′-[(4-formylphenoxy)methyl]biphenyl-2-carbonitrile (1430399-27-1) + [1-(2-aminoethyl)-3-aminopropyl]trimethoxysilane (1760-24-3) → 4'-((4-((1E)-9,9-dimethoxy-10-oxa-2,5-diaza-9-silaundec-1-en-1-yl)phenoxy)methyl)[1,1'-biphenyl]-2-carbonitrile

Conditions	Yield
In toluene Inert atmosphere; Schlenk technique; Dean-Stark; Reflux;	85%

2-hydroxy-5-methylbenzaldehyde (613-84-3) + [1-(2-aminoethyl)-3-aminopropyl]trimethoxysilane (1760-24-3) → N-[N-(3-(trimethoxysilyl)propyl)ethylenediamine]-5-methylsalicylaldimine (1293408-56-6)

Conditions	Yield
With formic acid In ethanol for 6h; Reflux;	84%

Upstream product

• 107-15-3 ethylenediamine 
• 2530-87-2 3-Chloropropyltrimethoxysilan 
• 67-56-1 methanol 

Downstream Products

• 174083-66-0 n-2-vinylbenzylamino-ethyl-3-aminopropyltrimethoxysilane 
• 74956-86-8 N1,N1-bis[3-(trimethoxysilyl)propyl]-1,2-ethanediamine 

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