3069-25-8

Basic information

• Product Name: N-Methylaminopropyltrimethoxysilane
• Synonyms: 3-TRIMETHOXYSILYL PROPYLMETHYLAMINE;(3-METHYLAMINOPROPYL)TRIMETHOXYSILANE;1-Propanamine, N-methyl-3-(trimethoxysilyl)-;CM8620;Trimethoxy[3-(methylamino)propyl]silane 97%;dynasylan1110;n-methyl-3-(trimethoxysilyl)-1-propanamin;N-methyl-3-(trimethoxysilyl)-1-Propanamine
• CAS NO: 3069-25-8
• Molecular Formula: C₇H₁₉NO₃Si
• Molecular Weight: 193.32
• EINECS: 221-334-5
• Mol File: 3069-25-8.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 106 °C(lit.)
• Flash Point: 180 °F
• Appearance: /
• Density: 0.975 g/mL at 25 °C(lit.)
• Vapor Pressure: 2.448mmHg at 25°C
• Refractive Index: n20/D 1.421
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 10.75±0.10(Predicted)
• Water Solubility: Hydrolyzes in water.
• Sensitive: Moisture Sensitive
• BRN: 2072720
• CAS DataBase Reference: N-Methylaminopropyltrimethoxysilane(CAS DataBase Reference)
• NIST Chemistry Reference: N-Methylaminopropyltrimethoxysilane(3069-25-8)
• EPA Substance Registry System: N-Methylaminopropyltrimethoxysilane(3069-25-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-26/36
• RIDADR: UN 1993 / PGIII
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 3069-25-8(Hazardous Substances Data)

Usage

Uses

(3-Methylaminopropyl)trimethoxysilane is used as coupling agent, adhesion promoters

General Description

Trimethoxy[3-(methylamino)propyl]silane (MAPTMS) is an aminoalkyltrimethoxysilane that can be used for silanization surface immobilization.

InChI:InChI=1/C7H19NO3Si/c1-6-7(8-2)12(9-3,10-4)11-5/h7-8H,6H2,1-5H3

Synthetic route

methylamine (74-89-5) + 3-Chloropropyltrimethoxysilan (2530-87-2) → N-methyl-3-trimethoxysilylpropylamine (3069-25-8)

N-methyl-N-allylamine (627-37-2) + trimethoxysilane (2487-90-3) → N-methyl-3-trimethoxysilylpropylamine (3069-25-8) + C7H19NO3Si

Conditions	Yield
With platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex at 80℃; for 20h; Schlenk technique; Inert atmosphere; Overall yield = 93.2 %Spectr.; regioselective reaction;

glutaric anhydride, (108-55-4) + N-methyl-3-trimethoxysilylpropylamine (3069-25-8) → C12H25NO6Si

Conditions	Yield
In tetrahydrofuran at 20℃;	100%

2-Isocyanatoethyl methacrylate (30674-80-7) + N-methyl-3-trimethoxysilylpropylamine (3069-25-8) → 3,3-dimethoxy-7-methyl-8-oxo-2-oxa-7,9-diaza-3-silaundecan-11-yl methacrylate (1560012-77-2)

Conditions	Yield
at 60℃;	100%

N-methyl-3-trimethoxysilylpropylamine (3069-25-8) + hexafluoroglutaric anhydride (376-68-1) → C12H19F6NO6Si

Conditions	Yield
In tetrahydrofuran at 20℃; for 0.5h;	99%

N-methyl-3-trimethoxysilylpropylamine (3069-25-8) + epichlorohydrin (106-89-8) → N-(2',3'-epoxypropyl)-(3-N-methylaminopropyl)-trimethoxysilane

Conditions	Yield
With potassium carbonate In toluene for 16h; Reflux; Inert atmosphere;	96%

N-methyl-3-trimethoxysilylpropylamine (3069-25-8) + hexafluoroglutaric anhydride (376-68-1) + silver(l) oxide (20667-12-3) → (H3CO)3Si(CH2)3N(CH3)C(O)(CF2)3COO(1-)*Ag(1+)=Ag[(H3CO)3Si(CH2)3N(CH3)C(O)(CF2)3COO] (876734-90-6)

Conditions	Yield
In further solvent(s) under Ar, Schlenk setup, glutaric anhydride (1.4 mmol) in MTBE added to soln. of silicon compd. (1.4 mmol), stirred for 10 min, added to Ag2O (1.4 mmol) suspd. in MTBE, stirred for 18 h at room temp. in darkness; evapd. (vac.), elem. anal.;	93%

N-methyl-3-trimethoxysilylpropylamine (3069-25-8) + acetyl chloride (75-36-5) → N-methyl-N-(3-(trimethoxysilyl)propyl)acetamide

Conditions	Yield
Stage #1: N-methyl-3-trimethoxysilylpropylamine With trimethylamine In dichloromethane at 0℃; for 0.166667h; Inert atmosphere; Stage #2: acetyl chloride In dichloromethane for 4.5h;	85%

N-methyl-3-trimethoxysilylpropylamine (3069-25-8) + bis(trifluoromethanesulfonyl)amide (82113-65-3) → C32H80N8O12Si8*8C2HF6NO4S2

Conditions	Yield
In water; dimethyl sulfoxide at 25 - 100℃; for 19h;	84%

N-methyl-3-trimethoxysilylpropylamine (3069-25-8) + 1,3-dibromo-propane (109-64-8) → N,N'-bis(trimethoxysilylpropyl)-N,N'-dimethyl-1,3-propanediamine

Conditions	Yield
at 130℃; for 3h; Inert atmosphere; Industrial scale;	80%

1,10-dichlorodecane (2162-98-3) + N-methyl-3-trimethoxysilylpropylamine (3069-25-8) → N,N'-bis(trimethoxysilylpropyl)-N,N'-dimethyl-1,10-decanediamine

Conditions	Yield
at 130℃; for 5h; Inert atmosphere;	78.8%

cyanoacetic acid chloride (16130-58-8) + N-methyl-3-trimethoxysilylpropylamine (3069-25-8) → N-methyl-N-(3-trimethoxysilyl propyl)cyanoacetamide

Conditions	Yield
With pyridine In diethyl ether at 20℃; for 2.5h;	75%
With pyridine In diethyl ether at 20℃; for 2.5h;	75%

1,5-dichloropentane (628-76-2) + N-methyl-3-trimethoxysilylpropylamine (3069-25-8) → N,N'-bis(trimethoxysilylpropyl)-N,N'-dimethyl-1,5-pentanediamine

Conditions	Yield
at 130℃; for 5h; Inert atmosphere;	74.8%

N-methyl-3-trimethoxysilylpropylamine (3069-25-8) + 1,3-Dichloropropane (142-28-9) → N,N'-bis(trimethoxysilylpropyl)-N,N'-dimethyl-1,3-propanediamine

Conditions	Yield
at 130℃; for 3h; Inert atmosphere; Industrial scale;	72.8%

N-methyl-3-trimethoxysilylpropylamine (3069-25-8) + 1,4-dichlorobutane (110-56-5) → N,N'-bis(trimethoxysilylpropyl)-N,N'-dimethyl-1,4-butanediamine

Conditions	Yield
at 130℃; for 5h; Inert atmosphere;	72.6%
at 130℃; for 5h; Inert atmosphere;	72.6%

1,12-diiodododecane (24772-65-4) + N-methyl-3-trimethoxysilylpropylamine (3069-25-8) → N,N'-bis(trimethoxysilylpropyl)-N,N'-dimethyl-1,12-dodecanediamine

Conditions	Yield
at 130℃; for 5h; Inert atmosphere;	67.5%

N-methyl-3-trimethoxysilylpropylamine (3069-25-8) + 1,3-chlorobromopropane (109-70-6) → N,N'-bis(trimethoxysilylpropyl)-N,N'-dimethyl-1,3-propanediamine

Conditions	Yield
at 130℃; for 3h; Inert atmosphere;	66.4%
at 130℃; for 3h; Inert atmosphere; Industrial scale;	66.4%

1,3,5,7,9,11,14-heptaisobutyltricyclo[7.3.3.15,11]heptasiloxane-endo-3,7,14-triol (307531-92-6) + N-methyl-3-trimethoxysilylpropylamine (3069-25-8) → N-(3-([heptaisobutyl]octasilsesquioxane)propyl)methanamine (1228187-76-5)

Conditions	Yield
With triethylamine In acetone for 48h; Reflux;	64.7%

N-methyl-3-trimethoxysilylpropylamine (3069-25-8) + 1,6-dichlorohexane (2163-00-0) → N,N'-bis(trimethoxysilylpropyl)-N,N'-dimethyl-1,6-hexanediamine

Conditions	Yield
at 130℃; for 5h; Concentration; Inert atmosphere;	60.9%

1,8-dibromooctane (4549-32-0) + N-methyl-3-trimethoxysilylpropylamine (3069-25-8) → N,N'-bis(trimethoxysilylpropyl)-N,N'-dimethyl-1,8-octanediamine

Conditions	Yield
at 130℃; for 5h; Inert atmosphere;	41.7%

1,7-dichloroheptane (821-76-1) + N-methyl-3-trimethoxysilylpropylamine (3069-25-8) → N,N'-bis(trimethoxysilylpropyl)-N,N'-dimethyl-1,7-heptanediamine

Conditions	Yield
at 130℃; for 5h; Inert atmosphere;	40.5%

thirane (420-12-2) + N-methyl-3-trimethoxysilylpropylamine (3069-25-8) → N-Methyl-N-(3-trimethoxy-silylpropyl)-2-amino-ethanthiol (18107-13-6)

Conditions	Yield
In 1,4-dioxane

N-methyl-3-trimethoxysilylpropylamine (3069-25-8) → methyl-(3-trifluorosilanyl-propyl)-amine; compound with trifluoroborane

Conditions	Yield
With boron trifluoride diethyl etherate

4-fluorobenzylidenemalononitrile (2826-22-4) + N-methyl-3-trimethoxysilylpropylamine (3069-25-8) → C17H23N3O3Si

Conditions	Yield
In various solvent(s)

1,5-difluoro-2,4-dinitrobenzene (327-92-4) + N-methyl-3-trimethoxysilylpropylamine (3069-25-8) → C13H20FN3O7Si

Conditions	Yield
In various solvent(s) at 50℃; for 0.5h;

1,5-difluoro-2,4-dinitrobenzene (327-92-4) + N-methyl-3-trimethoxysilylpropylamine (3069-25-8) → C20H38N4O10Si2

Conditions	Yield
In various solvent(s) at 130℃; for 2h;

N-methyl-3-trimethoxysilylpropylamine (3069-25-8) + (1E,4E)-1,5-bis(4-fluorophenyl)penta-1,4-dien-3-one (33386-21-9, 53369-00-9) → C24H30FNO4Si

Conditions	Yield
In various solvent(s)

N-methyl-3-trimethoxysilylpropylamine (3069-25-8) → T8-(CH2CH2CH2NHCH3)8 + T10-(CH2CH2CH2NHCH3)10 + T12-(CH2CH2CH2NHCH3)12

Conditions	Yield
With water In propan-1-ol at 60℃;

N-methyl-3-trimethoxysilylpropylamine (3069-25-8) + 1-fluoro-2-nitro-4-[(E)-2-(4-nitrophenyl)vinyl]-benzene (1221231-36-2) → C21H27N3O7Si (1221231-39-5)

Conditions	Yield
With tetraethoxy orthosilicate for 5h; Inert atmosphere; Reflux;

Upstream product

• 627-37-2 N-methyl-N-allylamine 
• 2487-90-3 trimethoxysilane 
• 74-89-5 methylamine 
• 2530-87-2 3-Chloropropyltrimethoxysilan 

Downstream Products

• 1228187-76-5 N-(3-([heptaisobutyl]octasilsesquioxane)propyl)methanamine 
• 1221231-39-5 C₂₁H₂₇N₃O₇Si 

Relevant articles and documents

Study of Karstedt's Catalyst for Hydrosilylation of a Wide Variety of Functionalized Alkenes with Triethoxysilane and Trimethoxysilane

The hydrosilylation is one of the most important methods for the synthesis of organosilicon compounds. Karstedt's catalyst [Ptn(H2C=CHSiMe2OSiMe2CH=CH2)m] is a kind of platinum catalyst which is widely used in the hydrosilylation. In this paper, we studied the catalytic activity of Karstedt's catalyst for the hydrogenation of olefins and especially aminated alkenes with trimethoxysilane and triethoxysilane, and demonstrated the excellent performance in terms of the yield and selectivity.

N-substituted (3-aminopropyl)trifluorosilanes and [3-(trifluorosilyl)propyl]diorganylamine-trifluoroboranes

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Azido-silane compositions

Azido-containing silane compositions of matter useful as coupling agents in the production of polymer composite articles.