3068-76-6

Basic information

• Product Name: N-[3-(TRIMETHOXYSILYL)PROPYL]ANILINE
• Synonyms: N-[.gamma.-(Trimethoxysilyl)propyl]aniline;n-[3-(trimethoxysilyl)propyl]-benzenamin;N-[3-(trimethoxysilyl)propyl]-Benzenamine;(3-ANILINOPROPYL)TRIMETHOXYSILANE;3-(PHENYLAMINO)PROPYLTRIMETHOXYSILANE;N-[3-(TRIMETHOXYSILYL)PROPYL]ANILINE;N-PHENYLAMINOPROPYLTRIMETHOXYSILANE;N-PHENYL-3-AMINOPROPYLTRIMETHOXYSILANE
• CAS NO: 3068-76-6
• Molecular Formula: C₁₂H₂₁NO₃Si
• Molecular Weight: 255.39
• EINECS: 221-328-2
• Product Categories: Si (Classes of Silicon Compounds);Si-O Compounds;Trialkoxysilanes;Amino Silanes
• Mol File: 3068-76-6.mol
• Article Data: 2

Chemical Properties

• Melting Point: <0°C
• Boiling Point: 310 °C(lit.)
• Flash Point: >230 °F
• Appearance: Yellowish clear liquid
• Density: 1.07 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.002mmHg at 25°C
• Refractive Index: n20/D 1.506(lit.)
• PKA: 5.02±0.50(Predicted)
• Water Solubility: 993-1000000mg/L at 20℃
• Sensitive: Moisture Sensitive
• BRN: 8620045
• CAS DataBase Reference: N-[3-(TRIMETHOXYSILYL)PROPYL]ANILINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-[3-(TRIMETHOXYSILYL)PROPYL]ANILINE(3068-76-6)
• EPA Substance Registry System: N-[3-(TRIMETHOXYSILYL)PROPYL]ANILINE(3068-76-6)

Safety Data

• Hazard Codes: C
• Statements: 34-40-48/20/21/22-52/53-68-43
• Safety Statements: 26-36/37/39-45-35
• RIDADR: UN 3267 8/PG 2
• WGK Germany: 1
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 3068-76-6(Hazardous Substances Data)

Usage

Chemical Properties

Yellowish clear liquid

Uses

TMSPA is a monomer which can be polymerized to form poly(TMPSA). Poly(TMPSA) can be used to coat gold nanorods (AuNRs) to fabricate an electrode for the sensing of hydrogen peroxide.

General Description

N-(3-(Trimethoxysilyl)propyl)aniline (TMSPA) is an organoalkoxysilane derivative of polyaniline (PAN). TMSPA is a pH sensitive silica-polyaniline hybrid which is electroactive and electrochromic in nature. It is used as a silane coupling agent.

InChI:InChI=1/C12H21NO3Si/c1-5-12(17(14-2,15-3)16-4)13-11-9-7-6-8-10-11/h6-10,12-13H,5H2,1-4H3

Synthetic route

aniline (62-53-3) + 3-Chloropropyltrimethoxysilan (2530-87-2) → N-phenyl-N-(3-trimethoxysilylpropyl)amine (3068-76-6)

Conditions	Yield
With polyaniline at 160℃; for 5h;	90.1%
at 90 - 100℃; for 8h;

2-Isocyanatoethyl methacrylate (30674-80-7) + N-phenyl-N-(3-trimethoxysilylpropyl)amine (3068-76-6) → 3,3-dimethoxy-8-oxo-7-phenyl-2-oxa-7,9-diaza-3-silaundecan-11-yl methacrylate

Conditions	Yield
at 50℃;	100%

acrylic acid 2-isocyanatoethyl ester (13641-96-8) + N-phenyl-N-(3-trimethoxysilylpropyl)amine (3068-76-6) → 3,3-dimethoxy-8-oxo-7-phenyl-2-oxa-7,9-diaza-3-silaundecan-11-yl acrylate

Conditions	Yield
at 45℃;	100%

2,3-Epoxypropyl methacrylate (106-91-2) + N-phenyl-N-(3-trimethoxysilylpropyl)amine (3068-76-6) → 2-hydroxy-3-(phenyl(3-(trimethoxysilyl)propyl)amino)propyl methacrylate

Conditions	Yield
With dmap; dibutyltin dilaurate at 20℃;	100%

(2-oxo-1,3-dioxolane-4-yl)methyl methacrylate (13818-44-5) + N-phenyl-N-(3-trimethoxysilylpropyl)amine (3068-76-6) → 11-hydroxy-3,3-dimethoxy-8-oxo-7-phenyl-2,9-dioxa-7-aza-3-siladodecan-12-yl methacrylate

Conditions	Yield
at 20℃;	100%

4-heptylbenzoyl chloride (50606-96-7) + N-phenyl-N-(3-trimethoxysilylpropyl)amine (3068-76-6) → C26H39NO4Si

Conditions	Yield
With triethylamine In toluene at 5 - 20℃; for 1.5h;	99%

C23H20ClNO4S + N-phenyl-N-(3-trimethoxysilylpropyl)amine (3068-76-6) → C35H40N2O7SSi

Conditions	Yield
In chloroform at 40 - 80℃; for 12h;	43%

N-phenyl-N-(3-trimethoxysilylpropyl)amine (3068-76-6) → phenyl-(3-trifluorosilanyl-propyl)-amine; compound with trifluoroborane

Conditions	Yield
With boron trifluoride diethyl etherate

phenyl isocyanate (103-71-9) + N-phenyl-N-(3-trimethoxysilylpropyl)amine (3068-76-6) → C19H26N2O3Si

Conditions	Yield
at 20 - 70℃;

methanol (67-56-1) + formaldehyd (50-00-0) + N-phenyl-N-(3-trimethoxysilylpropyl)amine (3068-76-6) → N-(methoxymethyl)-N-phenyl-N-(3-trimethoxysilylpropyl)amine (1440530-99-3)

Conditions	Yield
at 65℃; for 1h; Inert atmosphere;
at 65℃; for 1h; Inert atmosphere;

benzene-1,2-diol (120-80-9) + diisopropylamine (108-18-9) + N-phenyl-N-(3-trimethoxysilylpropyl)amine (3068-76-6) → diisopropylammonium bis(catecholato)(3-anilinopropyl)silicate

Conditions	Yield
Stage #1: benzene-1,2-diol; diisopropylamine In tetrahydrofuran at 20℃; for 0.25h; Inert atmosphere; Sealed tube; Stage #2: N-phenyl-N-(3-trimethoxysilylpropyl)amine In tetrahydrofuran at 75℃; for 16h; Inert atmosphere; Sealed tube;
Inert atmosphere; Autoclave; Reflux;

N-phenyl-N-(3-trimethoxysilylpropyl)amine (3068-76-6) → 2,2-dimethoxy-1-phenyl-1-aza-2-silacyclopentane

Conditions	Yield
With trifluorormethanesulfonic acid; 1,1,1,3,3,3-hexamethyl-disilazane In toluene for 4h; Reflux;

triethanolamine (102-71-6) + N-phenyl-N-(3-trimethoxysilylpropyl)amine (3068-76-6) → 1-N-phenylaminopropyl silatrane (85952-93-8)

Conditions	Yield
With potassium hydroxide In toluene for 5h;

2-isocyanato-2-methylpropane-1,3-diyl diacrylate (886577-76-0) + N-phenyl-N-(3-trimethoxysilylpropyl)amine (3068-76-6) → C23H34N2O8Si

Conditions	Yield
With dibutyltin dilaurate In butanone at 35℃; for 0.5h;

chloro-trimethyl-silane (75-77-4) + N-phenyl-N-(3-trimethoxysilylpropyl)amine (3068-76-6) → 3-(N-phenyl-N-trimethylsilylamino)propyltrimethoxysilane

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 50 - 60℃; for 4h; Reagent/catalyst; Inert atmosphere;	97.94 %Chromat.

Upstream product

• 62-53-3 aniline 
• 2530-87-2 3-Chloropropyltrimethoxysilan 

Downstream Products

• 85952-93-8 1-N-phenylaminopropyl silatrane 
• 1440530-99-3 N-(methoxymethyl)-N-phenyl-N-(3-trimethoxysilylpropyl)amine 

Relevant articles and documents

Preparation method for anilinopropylalkoxysilane

The invention provides a preparation method for anilinopropylalkoxysilane. The preparation method is characterized by comprising the steps of: under a condition of 130-180 DEG C, adding poly aniline, aniline and chloropropylalkoxysilane into a reactor; after a substitution reaction is finished, rectifying a filtered and separated liquid phase to obtain chloropropylalkoxysilane and excessive aniline, wherein the excessive aniline is recycled; and after regenerative treatment on the filtered and separated polyaniline such as neutralization and drying, recycling an obtained deacid agent. The yield of anilinopropylalkoxysilane reaches over 85%, and the selectivity of the anilinopropylalkoxysilane is greater than 90%.