13822-56-5

Basic information

• Product Name: 3-(Trimethoxysilyl)-1-propanamine
• Synonyms: 1-Propanamine,3-(trimethoxysilyl)-;3-(trimethoxysilyl)-1-propanamin;Aminopropyltrimethoxysilane;CA0880;Dynasylan AMMO;KBE 903;N-(Trimethoxysilylpropyl)amine;Propylamine, 3-(trimethoxysilyl)-
• CAS NO: 13822-56-5
• Molecular Formula: C₆H₁₇NO₃Si
• Molecular Weight: 179.29
• EINECS: 237-511-5
• Product Categories: Industrial/Fine Chemicals;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;Chemical Synthesis;Contact Printing;Materials Science;Micro/NanoElectronics;Organometallic Reagents;Organosilicon;Self Assembly &Self-Assembly Materials;Silanes
• Mol File: 13822-56-5.mol
• Article Data: 22

Chemical Properties

• Melting Point: 194°C
• Boiling Point: 91-92 °C15 mm Hg(lit.)
• Flash Point: 182 °F
• Appearance: Clear colorless/Liquid
• Density: 1.027 g/mL at 25 °C(lit.)
• Vapor Pressure: 4.314mmHg at 25°C
• Refractive Index: n20/D 1.424(lit.)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 10.61±0.10(Predicted)
• Water Solubility: reacts
• Sensitive: Moisture Sensitive
• Stability: Stable, but moisture sensitive. Incompatible with water, strong acids, strong oxidizing agents. Combustible.
• BRN: 2038118
• CAS DataBase Reference: 3-(Trimethoxysilyl)-1-propanamine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(Trimethoxysilyl)-1-propanamine(13822-56-5)
• EPA Substance Registry System: 3-(Trimethoxysilyl)-1-propanamine(13822-56-5)

Safety Data

• Hazard Codes: Xi,C
• Statements: 36/38-34-41-38
• Safety Statements: 26-45-36/37/39-25-39
• RIDADR: 3267
• WGK Germany: 3
• F: 1-10
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 13822-56-5(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 13822-56-5 differently. You can refer to the following data:
1. 3-(Trimethoxysilyl)-1-propanamine is an amino-functional silane that may be used over a broad range of applications to give an improvement in the bond between a substrate, filler or reinforcement and resins that react with the amino group. 3-(Trimethoxysilyl)-1-propanamine is especially recommended to thermoplastic resins and thermosetting resins such as epoxy, PBT, polyurethane etc. It can improve reinforced plastic's physical properties and electric properties as flexural strength, compression strength and shear strength. It also can improve the dispersion and wet ability of filler in the high molecular materials. 3-(TRIMETHOXYSILYL)-1-PROPANAMINE is an excellent promoter of adhesion and sealant (such as polyurethane, epoxy, and phenol). In the glass wool and FRP products, it can be added into phenol resins to improve the wet resistance and mechanical performance. Applications: Superior adhesion promoter in RTV silicones and other hybrid sealants. Excellent adhesion promoter for difficult substrates such as ABC, PVC ad Poly Shyrene. Useful component in primer systems for hybrid and polyurethane sealants.
2. (3-Aminopropyl)trimethoxysilane is used as a silane coupling agent on silver nanoparticles. It is also used in silanization processes. It is also used to prepare surface modified titanate nanotubes (TiNT).

Chemical Properties

Colorless transparent liquid

General Description

(3-Aminopropyl)trimethoxysilane(APTMS) is an amino-silane that is mainly used as a silane coupling agent for the surface modification of a variety of nanomaterials. APTMS based films form a thermally stable layer on different substrates.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C6H17NO3Si/c1-5-6(7)11(8-2,9-3)10-4/h6H,5,7H2,1-4H3

Synthetic route

trimethoxysilane (2487-90-3) + Triethoxysilane (998-30-1) → beta-amminopropyl trimethoxy silane (130530-83-5) + 3-(trimethoxysilyl)propan-1-amine (13822-56-5)

Conditions	Yield
	A 70% B n/a

trimethoxysilane (2487-90-3) + Triethoxysilane (998-30-1) → beta-aminopropyl triethoxy silane (53218-21-6) + 3-(trimethoxysilyl)propan-1-amine (13822-56-5)

Conditions	Yield
	A 62% B n/a
	A 62% B n/a

3-Chloropropyltrimethoxysilan (2530-87-2) → 3-(trimethoxysilyl)propan-1-amine (13822-56-5)

Conditions	Yield
With ammonia

methanol (67-56-1) + C9H23NO4Si (727425-61-8) → 2-ethoxy-ethanol (110-80-5) + 3-(trimethoxysilyl)propan-1-amine (13822-56-5)

Conditions	Yield
at 20℃; Kinetics; Equilibrium constant;

trimethoxysilane (2487-90-3) + 1-amino-2-propene (107-11-9) → beta-aminoisopropyltrimethoxysilane (50602-95-4) + 3-(trimethoxysilyl)propan-1-amine (13822-56-5)

Conditions	Yield
With platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex at 80℃; for 20h; Catalytic behavior; Schlenk technique; Inert atmosphere; Overall yield = 94.3 %Spectr.; regioselective reaction;

glutaric anhydride, (108-55-4) + 3-(trimethoxysilyl)propan-1-amine (13822-56-5) → C11H23NO6Si

Conditions	Yield
In tetrahydrofuran at 20℃; for 12h;	100%

1-Bromonaphthalene (90-11-9) + 3-(trimethoxysilyl)propan-1-amine (13822-56-5) → Methyl 1-naphthylphosphinate (145051-67-8)

Conditions	Yield
With anilinium hypophosphorous salt; 1,3-bis-(diphenylphosphino)propane; palladium diacetate In acetonitrile Heating;	100%

5-isothiocyanato-1,10-phenanthroline (75618-99-4) + 3-(trimethoxysilyl)propan-1-amine (13822-56-5) → N-(1,10-phenanthrolin-5-yl)-N'-(3-trimethoxysilylpropyl)thiourea (909109-37-1)

Conditions	Yield
In dichloromethane; pentane at 0℃; for 0.166667h;	100%

3-(trimethoxysilyl)propan-1-amine (13822-56-5) + 1-[(2-oxazepan-1-yl)carbonyl]azepan-2-one (19494-73-6) → caprolactam (105-60-2) + n-[5-(trimethoxysilyl)-2-aza-1-oxo-pentyl]caprolactam

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

acrylic acid-2-[N-methyl][(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)-1-sulfonylamino]-ethyl ester (49859-70-3) + 3-(trimethoxysilyl)propan-1-amine (13822-56-5) → C35H47F26N3O11S2Si

Conditions	Yield
at 70℃; for 5h;	100%

maleic anhydride (108-31-6) + 3-(trimethoxysilyl)propan-1-amine (13822-56-5) → C10H19NO6Si

Conditions	Yield
In dichloromethane at 20℃; for 1h;	99.1%

carbon disulfide (75-15-0) + 3-(trimethoxysilyl)propan-1-amine (13822-56-5) → C7H16NO3S2Si(1-)*Li(1+)

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

carbon disulfide (75-15-0) + 3-(trimethoxysilyl)propan-1-amine (13822-56-5) → C7H16NO3S2Si(1-)*K(1+)

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

3-(trimethoxysilyl)propan-1-amine (13822-56-5) + carbonic acid dimethyl ester (616-38-6) → N-(3-trimethoxysilylpropyl) O-methyl carbamate (23432-62-4)

Conditions	Yield
With sodium methylate In methanol at 55 - 80℃; for 3.5h; Temperature; Time;	99%
With sodium methylate In methanol at 55 - 80℃; for 4h; Large scale;	99%
With 8Na(1+)*12C4H10NO(1-)*2HO(1-)*2Nd(3+) In neat (no solvent) at 80℃; for 12h; Inert atmosphere; Schlenk technique; Green chemistry;	90%

succinic acid anhydride (108-30-5) + 3-(trimethoxysilyl)propan-1-amine (13822-56-5) → 4-oxo-4-[3-(trimethoxysilyl)propylamino]butanoic acid (342573-66-4)

Conditions	Yield
In tetrahydrofuran at -5 - 5℃; for 6h; Inert atmosphere;	99%
Inert atmosphere;	98%
In tetrahydrofuran at 20℃; for 18h; Inert atmosphere;

Pyridine-2,3-dicarboxylic anhydride (699-98-9) + 3-(trimethoxysilyl)propan-1-amine (13822-56-5) → C13H20N2O6Si

Conditions	Yield
In tetrahydrofuran at -5 - 5℃; for 5h; Inert atmosphere;	99%

3-(trimethoxysilyl)propan-1-amine (13822-56-5) + trimellitic Anhydride (552-30-7) → C15H21NO8Si (1204776-58-8)

Conditions	Yield
In tetrahydrofuran at -5 - 5℃; for 6h; Inert atmosphere;	99%

3-(trimethoxysilyl)propan-1-amine (13822-56-5) + urea (57-13-6) → 3-(trimethoxysilyl)propyl isocyanate (15396-00-6)

Conditions	Yield
Stage #1: 3-(trimethoxysilyl)propan-1-amine; urea With Trimethyl orthoacetate In dimethyl sulfoxide at 90 - 95℃; for 9h; Stage #2: With sulfuric acid; copper(II) oxide In dimethyl sulfoxide at 75 - 80℃; for 4.5h; pH=6.5; Concentration; Temperature; pH-value;	98.2%
Stage #1: 3-(trimethoxysilyl)propan-1-amine; urea In methanol at 180℃; under 8250.83 - 10501.1 Torr; for 12.5h; Stage #2: With tin(ll) chloride at 195℃; under 56.2556 Torr;	92%

ethanol (64-17-5) + 3-(trimethoxysilyl)propan-1-amine (13822-56-5) + sodium hydroxide (1310-73-2) + copper dichloride → copper sodium γ-aminopropylsiloxane + sodium chloride (7647-14-5)

Conditions	Yield
In methanol; water Si-compd. dissoln. in MeOH, aq. soln. of NaOH addn., refluxing (1 h), soln. of Cu-compd. in MeOH addn., refluxing (30 min), MeOH distillation off with simultaneous addn. of EtOH; NaCl filtration off, solvent removing; elem. anal.;	A 93% B 98%

3-(trimethoxysilyl)propan-1-amine (13822-56-5) → C3H8F4NSi(1-)*H3N*H(1+)

Conditions	Yield
With ammonium hydrogen difluoride In water at 20℃;	98%

[2-(acryloyloxy)ethyl]trimethylammonium bis-(trifluoromethane)sulfonimide (827027-31-6) + 3-(trimethoxysilyl)propan-1-amine (13822-56-5) → [2-{3-(3-trimethoxysilylpropylamino)propionyloxy}ethyl]-N,N,N-trimethylammonium bistrifluoromethanesulfonimide

Conditions	Yield
In acetonitrile at 20℃; for 5h;	97.6%

3-(trimethoxysilyl)propan-1-amine (13822-56-5) + C30H26N4O5Si2 (142721-70-8) → C32H48N2O11Si4

Conditions	Yield
In toluene Heating;	97%

carbon disulfide (75-15-0) + 3-(trimethoxysilyl)propan-1-amine (13822-56-5) → C7H16NO3S2Si(1-)*Na(1+)

Conditions	Yield
With sodium hydride In tetrahydrofuran at 0 - 65℃; Product distribution; Further Variations:; Reagents; Solvents; Temperatures;	97%

3-(trimethoxysilyl)propan-1-amine (13822-56-5) + Benzoyl isothiocyanate (532-55-8) → BTU-TMS

Conditions	Yield
In dichloromethane at 5℃; Inert atmosphere;	97%
In dichloromethane at 5 - 20℃; Inert atmosphere;	97%

3-(trimethoxysilyl)propan-1-amine (13822-56-5) + trans-4-(4-Heptylcyclohexyl)benzoesaeurechlorid (81930-19-0) → C26H45NO4Si

Conditions	Yield
With triethylamine In toluene at 5 - 20℃; for 17.5h;	97%

3-(trimethoxysilyl)propan-1-amine (13822-56-5) + trifluoroacetic acid (76-05-1) → octakis-(3-aminopropyl)octasilsesquioxane trifluoroacetic acid

Conditions	Yield
In water at 20℃; for 2h; Inert atmosphere; Schlenk technique;	97%

3-(trimethoxysilyl)propan-1-amine (13822-56-5) + bis(trifluoromethanesulfonyl)amide (82113-65-3) → C24H64N8O12Si8*8C2HF6NO4S2

Conditions	Yield
In water; dimethyl sulfoxide at 25 - 100℃; for 19h;	97%

2-dimethylaminoethyl isothiocyanate (7097-89-4) + 3-(trimethoxysilyl)propan-1-amine (13822-56-5) → 1-(2-Dimethylamino-ethyl)-3-(3-trimethoxysilyl-propyl)-thiourea (1065667-58-4)

Conditions	Yield
In 1,4-dioxane at 20℃; for 20h; Heating / reflux;	96.6%

carbon disulfide (75-15-0) + 3-(trimethoxysilyl)propan-1-amine (13822-56-5) → 3-(trimethoxysilyl)propyl isothiocyanate

Conditions	Yield
Stage #1: carbon disulfide; 3-(trimethoxysilyl)propan-1-amine In tetrahydrofuran at 0 - 5℃; for 3h; Addition; Stage #2: With CYANAMID; triethylamine In tetrahydrofuran at 40℃; for 3h; Elimination;	96%

3-(trimethoxysilyl)propan-1-amine (13822-56-5) + 3-hydroxy-1,2,3-benzotriazin-4(3H)-one ester of di-isopropylthio-acetic acid (156881-71-9) → C14H31NO4S2Si

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 4h;	96%

3-(trimethoxysilyl)propan-1-amine (13822-56-5) + 5,10,15-tri(4-tert-butylphenyl)-20-[4-(succinimidyloxycarbonyl)phenyl]porphyrin → 5,10,15-tri(4-tert-butylphenyl)-20-[4-(3-trimethoxysilylpropylaminocarbonyl)phenyl]-porphyrin

Conditions	Yield
In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Schlenk technique;	96%

2-bromoisobutyric acid bromide (20769-85-1) + 3-(trimethoxysilyl)propan-1-amine (13822-56-5) → 2-bromo-2-methyl-N-(3-trimethoxysilyl-propyl)-propionamide

Conditions	Yield
With triethylamine In dichloromethane for 14h;	95.1%
With triethylamine In dichloromethane for 2h; Cooling with ice; Inert atmosphere;

3-(trimethoxysilyl)propan-1-amine (13822-56-5) + p-(iodophenyl)carboxaldehyde (15164-44-0) → 4-iodobenzylidene-3-trimethoxylsilanylpropylamine

Conditions	Yield
In methanol for 20h; Heating;	95%

3-(trimethoxysilyl)propan-1-amine (13822-56-5) + phenyl isothiocyanate (103-72-0) → N-phenyl-N'-[3-(trimethoxysilyl)propyl]thiourea (155159-97-0)

Conditions	Yield
With triethylamine In dichloromethane for 24h;	95%
With triethylamine In chloroform at 50℃;

3-(trimethoxysilyl)propan-1-amine (13822-56-5) + butyl isothiocyanate (592-82-5) → N-butyl-N'-[3-(trimethoxysilyl)propyl]thiourea (127455-96-3)

Conditions	Yield
With triethylamine In dichloromethane for 24h;	95%

Upstream product

• 2487-90-3 trimethoxysilane 
• 998-30-1 Triethoxysilane 
• 107-11-9 1-amino-2-propene 
• 2530-87-2 3-Chloropropyltrimethoxysilan 
• 67-56-1 methanol 
• 727425-61-8 C₉H₂₃NO₄Si 

Downstream Products

• 17869-27-1 3-(2,8,9-trioxa-5-aza-1-sila-bicyclo[3.3.3]undec-1-yl)-propylamine 
• 105-60-2 caprolactam 
• 106996-32-1 n-[5-(trimethoxysilyl)-2-aza-1-oxo-pentyl]caprolactam 
• 23432-62-4 N-(3-trimethoxysilylpropyl) O-methyl carbamate 
• 17945-05-0 N-(3-triethoxysilylpropyl)-O-ethylcarbamate 
• 192389-48-3 N-(3-trimethoxy-silylpropyl)-aspartic acid diethyl ester 
• 26115-70-8 tris-[3-(trimethoxysilyl)propyl]isocyanurate 
• 7647-14-5 sodium chloride 
• 1187627-88-8 C₁₉H₂₇N₃O₆SSi 
• 1218774-97-0 C₃₁H₃₉F₁₇N₂O₁₀Si₂ 
• 1160705-20-3 4-diphenylphosphinylbenzenecarboxylic acid 4-[N-(3-trimethoxysilylpropyl)amide] 
• 119777-51-4 N-phenyl-N'-[3-(trimethoxysilyl)propyl]urea 
• 112926-00-8 silica gel 
• 1221231-37-3 C₁₉H₂₂FN₃O₆Si 

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