4147-89-1

Basic information

• Product Name: 1,1,1-trimethyl-N-phenyl-N-(trimethylsilyl)silanamine
• Synonyms: Aniline, N,N-bis(trimethylsilyl)-; Silanamine, 1,1,1-trimethyl-N-phenyl-N-(trimethylsilyl)-
• CAS NO: 4147-89-1
• Molecular Formula: C₁₂H₂₃NSi₂
• Molecular Weight: 237.4887
• Mol File: 4147-89-1.mol
• Article Data: 16

Chemical Properties

• Melting Point: 16.5°C
• Boiling Point: 248.3°C at 760 mmHg
• Flash Point: 104°C
• Density: 0.896g/cm³
• Vapor Pressure: 0.0244mmHg at 25°C
• Refractive Index: 1.489
• CAS DataBase Reference: 1,1,1-trimethyl-N-phenyl-N-(trimethylsilyl)silanamine(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1,1-trimethyl-N-phenyl-N-(trimethylsilyl)silanamine(4147-89-1)
• EPA Substance Registry System: 1,1,1-trimethyl-N-phenyl-N-(trimethylsilyl)silanamine(4147-89-1)

Safety Data

• Hazardous Substances Data: 4147-89-1(Hazardous Substances Data)

Usage

Type of compound

Silanamine derivative

Structure

A trimethylsilyl group attached to the nitrogen atom of a phenyl group

Common use

Reagent in organic synthesis

Specific application

Formation of silicon-containing molecules

Chemical properties

Ability to react with a variety of organic compounds

Versatility

Useful tool in synthetic chemistry

Potential applications

Field of materials science

Silicon-containing nature

Can impart unique properties to polymers and other materials

Safety

Proper handling and storage procedures should be followed

Upstream product

• 70557-64-1 O,O-diisopropyl S-(trimethylsilyl) phosphorodithioate 
• 222851-56-1 N-phenylsulfinylamine 
• 3768-55-6 N-trimethylsilylaniline 
• 996-50-9 N,N-diethyl-1,1,1-trimethylsilanamine 
• 108-86-1 bromobenzene 
• 4039-32-1 lithium hexamethyldisilazane 
• 108-90-7 chlorobenzene 
• 1070-89-9 sodium hexamethyldisilazane 
• 591-50-4 iodobenzene 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 108-88-3 toluene 
• 462-06-6 fluorobenzene 
• 98-95-3 nitrobenzene 
• 13032-12-7 1,1'-bis(trimethylsilyl)-1,1',4,4'-tetrahydro-4,4'-bipyridylidene 

Downstream Products

• 51907-86-9 2,2,4,4-Tetrafluoro-2,4-dimethyl-1,3-diphenyl-2λ⁵,4λ⁵-[1,3,2,4]diazadiphosphetidine 
• 109717-51-3 2,2,4,4-Tetrafluoro-1,2,3,4-tetraphenyl-2λ⁵,4λ⁵-[1,3,2,4]diazadiphosphetidine 
• 39652-39-6 2,4-dichloro-1,3-diphenyl-cyclodiphosphazane 
• 17591-49-0 2,4-Dimethyl-1,2,3,4-tetraphenyl-cyclodisilazan 
• 6002-71-7 N-Phenyl-chlorarsazan 
• 15199-01-6 2,2,2,4,4,4-Hexafluor-1,3-diphenyl-1,3,2,4-diazadiphosphetidin 
• 107-46-0 Hexamethyldisiloxane 
• 90756-34-6 benzenediazonium trifluoromethanesulfonate 
• 18246-56-5 trimethyl(isopentyloxy)silane 
• 71290-63-6 benzenediazonium bromide 
• 100-34-5 benzene diazonium chloride 
• 369-57-3 benzenediazonium tetrafluoroborate 
• 222851-56-1 N-phenylsulfinylamine 
• 62-53-3 aniline 

Relevant articles and documents

Photo electron transfer induced desilylation of: N, N -bis(trimethylsilyl)aminodibenzoborole to aminodibenzoborole

The synthesis of 9-amino-9-borafluorene is described using a photoinduced twofold desilylation of the N,N-bis(trimethylsilyl) derivative 2. The mechanistic analysis suggests an initial single electron transfer step from 2 to the halogen containing solvent. 9-Amino-9-borafluorene undergoes a photoinduced cyclooligomerization, most reasonably to the dimer.

Metal-free deoxygenation and reductive disilylation of nitroarenes by organosilicon reducing reagents

A metal-free deoxygenation and reductive disilylation of nitroarenes was achieved using N,N’-bis(trime-thylsilyl)-4,4’-bipyridinylidene (1) under mild and neutral reaction conditions, and a broad functional group tolerance was possible in this reaction. Mono-deoxygenation, giving a synthetically valuable N,O-bis(trimethylsilyl)phe-nylhydroxylamine (7a) as a readily available and safe phenylnitrene source from nitrobenzene, and double-deoxy-genation, giving N,N-bis(trimethylsilyl)anilines 8, were easily controlled by varying the amounts of 1 and reaction temperature as well as adding dibenzothiophene (DBTP). Reaction of 2-arylnitrobenzenes with 1 resulted in the formation of the corresponding carbazoles 14 via in situ-gen-erated phenylnitrene species derived by thermolysis of N,O-bis(trimethylsilyl)phenylhydroxylamines 7, followed by their subsequent intramolecular C H insertion. In addition, the intramolecular N N coupling reaction proceeded in the reduction of 2,2’-dinitrobiphenyl derivatives by 1, giving the corresponding benzo[c]cinnolines.

Peculiarities of the reaction of alkali metal bis(trimethylsilyl)amides with halobenzenes

Lithium and sodium bis(trimethylsilyl)amides react with fluoro-, bromo-, and chlorobenzenes in THF or toluene to give a mixture of N,N-bis(trimethylsilyl)aniline and N,2-bis(trimethylsilyl)aniline. The latter compound is resulted from 1,3-shift of the trimethylsilyl group from nitrogen to ortho-carbon atom of the benzene ring. Effects of the solvent, halogen, and alkali metal nature as well as the reaction conditions on the ratio of isomers were examined. Reaction of iodobenzene with sodium bis(trimethylsilyl)amide in THF produces N,N-bis(trimethylsilyl)aniline and 2-iodo-N,N-bis(trimethylsilyl)aniline, while in toluene a mixture of three products, two indicated above and N,N-bis(trimethylsilyl)benzylamine, was obtained.