53215-95-5

Basic information

• Product Name: N-[(Trimethylsilyl)methyl]benzylamine
• Synonyms: N-(TRIMETHYLSILYLMETHYL)BENZYAMINE;Benzyl(trimethylsilylmethyl)amine;N-(trimethylsilylmethyl)benzamine;N-benzyl-1-(trimethylsilyl)methanamine;N-Benzyl-1-(trimethylsilyl)methylamine;BenzeneMethanaMine, N-[(triMethylsilyl)Methyl]-;N-Benzyl-N-[(triMethylsilyl)Methyl]aMine;N-[(TriMethylsilyl)Methyl]benzylaMine 98%
• CAS NO: 53215-95-5
• Molecular Formula: C₁₁H₁₉NSi
• Molecular Weight: 193.36
• Product Categories: Amines and Anilines;Amines;C11 to C38;Nitrogen Compounds
• Mol File: 53215-95-5.mol
• Article Data: 40

Chemical Properties

• Boiling Point: 89-90 °C5 mm Hg(lit.)
• Flash Point: 205 °F
• Appearance: Pale yellow/Liquid
• Density: 0.88 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.015mmHg at 25°C
• Refractive Index: n20/D 1.496(lit.)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 9.29±0.20(Predicted)
• CAS DataBase Reference: N-[(Trimethylsilyl)methyl]benzylamine(CAS DataBase Reference)
• NIST Chemistry Reference: N-[(Trimethylsilyl)methyl]benzylamine(53215-95-5)
• EPA Substance Registry System: N-[(Trimethylsilyl)methyl]benzylamine(53215-95-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• TSCA: No
• Hazardous Substances Data: 53215-95-5(Hazardous Substances Data)

Usage

Description

N-[(Trimethylsilyl)methyl]benzylamine is a colorless liquid that serves as a useful intermediate in the synthesis of cyanoaminosilanes. These cyanoaminosilanes are then utilized as azomethine ylide equivalents, which are crucial in various chemical reactions and processes.

Uses

Used in Chemical Synthesis:
N-[(Trimethylsilyl)methyl]benzylamine is used as an intermediate in the production of cyanoaminosilanes for chemical synthesis. Its role in creating azomethine ylide equivalents is essential for facilitating a range of chemical reactions and processes.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, N-[(Trimethylsilyl)methyl]benzylamine may be used as a building block for the development of new drugs or drug candidates. Its ability to form azomethine ylides can be leveraged in the synthesis of complex molecular structures with potential therapeutic applications.
Used in Material Science:
N-[(Trimethylsilyl)methyl]benzylamine could also find applications in material science, particularly in the synthesis of novel materials with unique properties. The versatility of azomethine ylides in creating diverse chemical structures makes this compound a valuable asset in the development of advanced materials for various applications.

InChI:InChI=1/C10H17NSi/c1-12(2,3)9-11-10-7-5-4-6-8-10/h4-8,11H,9H2,1-3H3

Upstream product

• 100-46-9 benzylamine 
• 2344-80-1 Chloromethyltrimethylsilane 
• 59006-07-4 (trimethylsilyl)methyl 4-methylbenzenesulfonate 
• 4206-67-1 iodo(trimethylsilyl)methane 

Downstream Products

• 93102-05-7 N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine 
• 141538-58-1 N-benzyl-N-(4-methylbenzyl)(trimethylsilyl)methylamine 
• 93102-06-8 N-benzyl-N-(butyloxymethyl)trimethylsilylmethylamine 
• 127275-19-8 1-amino>-3-butene 
• 157667-91-9 1-amino>-1-phenyl-3-butene 
• 157667-92-0 1-amino>-1-phenyl-4-pentene 
• 87813-06-7 dimethyl 1-benzylpyrrolidine-3,4-dicarboxylate 
• 87813-05-6 dimethyl (3R,4R)-1-benzylpyrrolidine-3,4-dicarboxylate 
• 17012-21-4 1-benzylpyrrolidine-3-carboxylic acid methyl ester 
• 607741-39-9 benzyl-[1-(benzyl-trimethylsilanylmethyl-carbamoyl)-ethyl]-carbamic acid tert-butyl ester 
• 671777-77-8 N-benzyl-2-oxo-2-phenyl-N-trimethylsilanylmethyl-acetamide 
• 1026552-54-4 C₁₁H₁₈N₂OSi 
• 1029604-58-7 (R,E)-ethyl 2-(benzyl((trimethylsilyl)methyl)amino)-4-phenylbut-3-enoate 
• 1025025-18-6 1-benzyl-3-(3,5-dichlorophenyl)-3-(trifluoromethyl)pyrrolidine 

Relevant articles and documents

Stereo-, Regio-, and Chemoselective [3 + 2]-Cycloaddition of (2E,4E)-Ethyl 5-(Phenylsulfonyl)penta-2,4-dienoate with Various Azomethine Ylides, Nitrones, and Nitrile Oxides: Synthesis of Pyrrolidine, Isoxazolidine, and Isoxazoline Derivatives and a Computational Study

One-pot chemo-, regio-, and stereoselective synthesis of series of heterocyclic and spiroheterocyclic compounds was accomplished through mono- and bis[3 + 2]-cycloaddition reactions of (2E,4E)-ethyl 5-(phenylsulfonyl)penta-2,4-dienoate as a dipolarophile with azomethine ylides, nitrones, and nitrile oxides in good yields. The structures of the products were established by spectroscopic techniques as well as by single-crystal XRD study, and DFT calculations were performed to further understand the mechanism of this [3 + 2]-cycloaddition reaction.

A Photocatalyst-Free, SET-Mediated Photochemical Approach for the Synthesis of Dumbbell-Like Amine-Functionalized Bis-C 60 Fullerene through C-C Bond Formation

A novel method for the synthesis of dumbbell-like amine-functionalized bis-C 60 fullerene from simple bis-α-silyl tertiary benzyl amines and C 60 fullerene is described. The photoreactions between bis-α-silyl tertiary benzyl amines and C 60 furnished single-bonded bis-aminomethyl-1,2-dihyrofullerenes and double-bonded 1,2,5-trisubstituted bis-fulleropyrrolidines through 1,3-dipolar cycloaddition reactions of azomethine ylides under mild conditions.

N-Cyanation of Primary and Secondary Amines with Cyanobenzio-doxolone (CBX) Reagent

An efficient electrophilic N-cyanation of amines with a stable and less-toxic cyanobenziodoxole reagent towards the synthesis of cyanamides is disclosed. This synthetically practicable strategy allows the construction of a wide variety of cyanamides under very mild and simple conditions with a broad functional group compatibility, and showcases a huge potential in late-stage modification of complex molecules.

Metal-Free Aminomethylation of Aromatic Sulfones Promoted by Eosin Y

A metal-free α-aminomethylation of heteroaryls promoted by eosin Y under green light irradiation is reported. A large variety of α-trimethylsilylamines as precursor of α-aminomethyl radical species were engaged to functionalize sulfonyl-heteroaryls following a Homolytic Aromatic Substitution (HAS) pathway. This method has provided a range of α-aminoheteroaryl compounds including a functionalized natural product. The mechanism of this late-stage functionalization of aryls was investigated and suggests the formation of a sulfonyl radical intermediate over a reductive quenching cycle.