3069-29-2

Usage

Introduction

3-(2-Aminoethylamino)propyl-dimethoxymethylsilane is a colorless, strongly alkaline liquid with amine smell being very sensitive to hydrolysis. 3-(2-Aminoethylamino)propyl-dimethoxymethylsilane is a diamino-functional silane capable of providing good adhesion and superior elougation and flexibility at the polymer-substrate interface. It is used to promote adhesion between glass, mineral and metal surfaces - reinforcements, fillers and substrates - and resins that react with amino groups in systems such as PVC plastisol, polyurethane, or epoxy-based adhesives and sealant, or in phenolic and epoxy molding compounds. Its reduced alkoxy functionality might also be useful in waterborne systems such as latex coatings, adhesives and sealants, providing lower reactivity and therefore higher stability in the aqueous environment. Applications: 3-(2-Aminoethylamino)propyl-dimethoxymethylsilane can be used as adhesion promoters in polysulfide, polyvinyl chloride plastisol, silicone two-part urethanes and epoxy adhesives and sealants. Used as additives for cold-curing phenolic and furan foundry resins to improve the flexural strength of the sand-resin composites while; Used to maintain the shelf life of the resin over long periods; Used as starting material in the synthesis of amino-functional silicones; Used as additives to latex coatings, adhesives and sealants; Used as adhesion promoters in one-part silylated urethane adhesives and sealants.

Chemical Properties

Colorless transparent liquid

Flammability and Explosibility

Notclassified

Synthetic route

ethylenediamine (107-15-3) + 3-chloropropylmethyldimethoxysilane (18171-19-2) → N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane (3069-29-2)

Conditions	Yield
Stage #1: ethylenediamine; 3-chloropropylmethyldimethoxysilane for 6h; Stage #2: With ethanol; sodium at 80℃;	83%

ethyldiethanolamine (139-87-7) + N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane (3069-29-2) → 2-γ-N-(aminoethyl)aminopropyl-2-methyl-6-ethyl-1,3-dioxa-6-aza-2-silacyclooctane

Conditions	Yield
With sodium In toluene for 8h; Heating;	94%

2,2'-(n-propylimino)bisethanol (6735-35-9) + N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane (3069-29-2) → 2-γ-N-(aminoethyl)aminopropyl-2-methyl-6-propyl-1,3-dioxa-6-aza-2-silacyclooctane

Conditions	Yield
With sodium In toluene for 8h; Heating;	91%

N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane (3069-29-2) + 2,2'-iminobis[ethanol] (111-42-2) → 2-γ-N-(aminoethyl)aminopropyl-2-methyl-1,3-dioxa-6-aza-2-silacyclooctane

Conditions	Yield
With sodium In toluene for 8h; Heating;	89%

N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane (3069-29-2) + N-n-pentyldiethanolamine (52891-00-6) → 2-γ-N-(aminoethyl)aminopropyl-2-methyl-6-pentyl-1,3-dioxa-6-aza-2-silacyclooctane

Conditions	Yield
With sodium In toluene for 8h; Heating;	85%

N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane (3069-29-2) + 2,2'-(phenylimino)bis[ethanol] (120-07-0) → 2-γ-N-(aminoethyl)aminopropyl-2-methyl-6-phenyl-1,3-dioxa-6-aza-2-silacyclooctane

Conditions	Yield
With sodium In toluene for 8h; Heating;	84%

n-butyldiethanolamine (102-79-4) + N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane (3069-29-2) → 2-γ-N-(aminoethyl)aminopropyl-2-methyl-6-butyl-1,3-dioxa-6-aza-2-silacyclooctane

Conditions	Yield
With sodium In toluene for 8h; Heating;	73%

formaldehyd (50-00-0) + N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane (3069-29-2) + C30H23O9PS2 → C54H75N4O13PS2Si2

Conditions	Yield
In toluene at 80 - 85℃; for 28h; Inert atmosphere;	56%

Hexamethyldisiloxane (107-46-0) + N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane (3069-29-2) → N-(2-aminoethyl)-3-aminopropyltrisiloxane (72330-51-9)

Conditions	Yield
With tetramethyl ammoniumhydroxide at 90℃; for 2h; Inert atmosphere;	52.9%
With tetramethyl ammoniumhydroxide for 2h; Reflux; Inert atmosphere;	44.73%

citric acid chloride (85698-65-3) + N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane (3069-29-2) → C30H68N6O10Si3

Conditions	Yield
for 0.5h;	40.7%

octamethylcyclotetrasiloxane (556-67-2) + N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane (3069-29-2) → Reaxys ID: 11372000

Conditions	Yield
With tetra(n-butyl)ammonium hydroxide In methanol at 70 - 110℃; for 4.5h;

glycidyldiethylamine (2917-91-1) + 3-(dimethylamino)-1,2-propanediol (623-57-4) + 1-chloro-3-diethylaminopropan-2-ol (15285-59-3) + 1,3-bis(diethylamino)propan-2-ol (3492-47-5) + N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane (3069-29-2) → C22H52N4O4Si (850218-50-7) + C42H98N8O7Si2 (850218-51-8)

Conditions	Yield
at 60℃; for 6h;

(Z)-9-octadecenoyl chloride (112-77-6) + N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane (3069-29-2) → C26H54N2O3Si (873300-53-9)

Conditions	Yield
With pyridine In diethyl ether

N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane (3069-29-2) + Stearoyl chloride (112-76-5) → C26H56N2O3Si (1097833-24-3)

Conditions	Yield
With pyridine In diethyl ether

N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane (3069-29-2) + 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;

N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane (3069-29-2) + undecamethylpentasiloxane-1-ol → C28H82N2O10Si11 (1026780-26-6)

Conditions	Yield
Stage #1: N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane; undecamethylpentasiloxane-1-ol In toluene at 80 - 100℃; for 24h; Stage #2: With ammonium hydroxide

N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane (3069-29-2) + benzoyl chloride (98-88-4) → C15H26N2O3Si (1246886-40-7)

Conditions	Yield
With pyridine at 70℃; for 4h;

N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane (3069-29-2) + acetyl chloride (75-36-5) → C10H24N2O3Si (1246886-41-8)

Conditions	Yield
With pyridine at 70℃; for 4h;

strontium nitrate + terbium(III) nitrate hexahydrate + yttrium(lll) nitrate hexahydrate + N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane (3069-29-2) → Sr2Y8(SiO4)6O2#dotTb(3+)

Conditions	Yield
In water aq. solns. of Y, Tb and Sr salts mixed in stoich. ratio with stirring, H2N(CH2)2NH(CH2)3SiCH3(OCH3)2 added, gelated, dried (80°C); thermolysed at 1000°C for 4 h; detd. by SEM;

terbium(III) nitrate hexahydrate + yttrium(lll) nitrate hexahydrate + N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane (3069-29-2) + calcium(II) nitrate (13477-34-4) → Ca2Y8(SiO4)6O2#dotTb(3+)

Conditions	Yield
In water aq. solns. of Y, Tb and Ca salts mixed in stoich. ratio with stirring, H2N(CH2)2NH(CH2)3SiCH3(OCH3)2 added, gelated, dried (80°C); thermolysed at 1000°C for 4 h; detd. by SEM;

1,3-propanesultone (1120-71-4) + N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane (3069-29-2) → C11H28N2O6SSi (4515-09-7)

Conditions	Yield
In ethanol at 40℃; for 2h; Reflux;

N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane (3069-29-2) + Methacryloyl chloride (920-46-7) → C16H30N2O4Si (1414363-24-8)

Conditions	Yield
With triethylamine In toluene at 0 - 20℃; for 3h;

N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane (3069-29-2) → C12H34N2O2Si3*2C2H4O2

Conditions	Yield
Multi-step reaction with 2 steps 1: tetramethyl ammoniumhydroxide / 2 h / Reflux; Inert atmosphere 2: dichloromethane / 6 h / Reflux View Scheme

N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane (3069-29-2) → C12H34N2O2Si3*2C3H6O2

Conditions	Yield
Multi-step reaction with 2 steps 1: tetramethyl ammoniumhydroxide / 2 h / Reflux; Inert atmosphere 2: dichloromethane / 6 h / Reflux View Scheme

N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane (3069-29-2) → C12H34N2O2Si3*2C4H8O2

Conditions	Yield
Multi-step reaction with 2 steps 1: tetramethyl ammoniumhydroxide / 2 h / Reflux; Inert atmosphere 2: dichloromethane / 6 h / Reflux View Scheme

dimethyldimethoxysilan (1112-39-6) + N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane (3069-29-2) → N-β-aminoethyl-γ-aminopropylheptamethylcyclo-tetrasiloxane

Conditions	Yield
With potassium hydroxide In water; toluene at 20℃; for 4.5h;	9.78 g

N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane (3069-29-2) + 3-Chloropropyltrimethoxysilan (2530-87-2) → N-[3-(trimethoxysilyl)propyl]-N-[3-(methyldimethoxysilyl)propyl]ethylenediamine

Conditions	Yield
at 135℃; for 7h;	364.7 g

succinic acid (110-15-6) + N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane (3069-29-2) → C12H24N2O8SSi(2-)*2Na(1+)

Conditions	Yield
Stage #1: succinic acid; N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane at 80 - 100℃; Stage #2: With sodium sulfite at 80 - 100℃;

N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane (3069-29-2) → C25H70N10O5Si5

Conditions	Yield
With sodium hydroxide In water

Upstream product

• 107-15-3 ethylenediamine 
• 18171-19-2 3-chloropropylmethyldimethoxysilane 

Downstream Products

• 1246886-40-7 C₁₅H₂₆N₂O₃Si 

Relevant academic research and scientific papers

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Cleavage of cyclic organosilanes in the preparation of aminofunctional organoalkoxysilanes

An aminofunctional organoalkoxysilane of formula I R2N—(CH2)y—Si(OR1)3?nR2n ??(I), wherein the R groups bonded to nitrogen are identical or different and each individual R group is hydrogen, an alkyl radical having from 1 to 4 carbon atoms, an aryl radical or an arylalkyl radical, R1 is an alkyl radical having from 1 to 8 carbon atoms or an aryl radical, R2 is an alkyl radical having from 1 to 8 carbon atoms or an aryl radical, y is 2, 3 or 4 and n is 0, 1 or 2, is prepared by a process comprising: reacting a chlorofunctional organoalkoxysilane of formula II Cl—(CH2)y—Si(OR1)3?nR2n ??(II), wherein R1, R2, y and n are as defined above, with ammonia or an organic amine of formula III HNR2 ??(III), wherein the two R groups are identical or different and each is defined as described above; separating organic amine hydrochloride or ammonium chloride by-product which is formed in the reaction; distilling the resulting crude product, thereby preparing an aminofunctional organoalkoxysilane or the product fraction of an aminofunctional organoalkoxysilane; and treating the aminofunctional organoalkoxysilane or the product fraction of an aminofunctional organoalkoxysilane with an alcohol.

Synthesis of 2-γ-N-(aminoethyl)aminopropyl-2-methyl-6-alkyl(aryl,H)-1,3-dioxa-6- aza-2-silacyclooctanes

Some new 2-γ-N-(aminoethyl)aminopropyl-2-methyl-1,3-dioxa-6-aza-2- silacyclooctane and 2-γ-N-(aminoethyl)aminopropyl-2-methyl-6-alkyl(aryl)-1,3-dioxa-6-aza- 2-silacyclooctanes have been synthesized from γ-chloropropyldimethoxymethyl silane by ethylenediamine substitution and diethanolamine or N-alkyl(aryl)diethanolamines substitution. The resulting silocanes have been characterized by elemental analyses, IR, and 1H NMR.