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

• 75-77-4 chloro-trimethyl-silane 
• 3768-55-6 N-trimethylsilylaniline 
• 40347-05-5 diethylaluminium-(N-phenyl-trimethylsilyl)amide 
• 103-71-9 phenyl isocyanate 
• 62-53-3 aniline 
• 996-50-9 N,N-diethyl-1,1,1-trimethylsilanamine 
• 70557-64-1 O,O-diisopropyl S-(trimethylsilyl) phosphorodithioate 
• 222851-56-1 N-phenylsulfinylamine 
• 108-86-1 bromobenzene 
• 4039-32-1 lithium hexamethyldisilazane 
• 1070-89-9 sodium hexamethyldisilazane 
• 98-95-3 nitrobenzene 
• 591-50-4 iodobenzene 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 

Downstream Products

• 3284-06-8 N,N'-diphenyltetramethylcyclodisilazane 
• 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 
• 62-53-3 aniline 
• 21597-12-6 N-phenyl-1,2,4-dithiazolidine-3,5-dione 
• 77541-96-9 S-trichloromethyl dithiopercarbanilidate 
• 20440-95-3 N-phenyl-di-p-tolylamine 
• 38166-95-9 N-phenyl-N-trimethylsilylbenzamide 
• 845254-79-7 [Ti(N-phenyl)Cl(μ-Cl)(THF)2]2 
• 81720-62-9 3,5-diphenylcyclo-1-oxa-3,5-diaza-2,4,6-trimethyl-2,4,6-triborane 

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.

Simple Nickel Salts for the Amination of (Hetero)aryl Bromides and Iodides with Lithium Bis(trimethylsilyl)amide

Recent developments in the chemistry of C-N bond formation and the synthesis of anilines have allowed for the use of first-row transition metals to catalyze these transformations. Much of the progress in this area has been driven by comprehensive screening for privileged/tailored ligands, which can be costly and not readily available in a research laboratory setting. In this communication we report a protocol in which simple nickel salts catalyze the C-N cross-coupling reaction between (hetero)aryl bromides and iodides with lithium bis(trimethylsilyl)amide without the need for any additive ligand. This method is amenable to low nickel catalyst loadings (1%) as well as gram-scale reactions. Because of the good functional group tolerance and compatibility with heterocyclic moieties, this method is useful for academic laboratory settings where access to tailored ligands and noble-metal catalysts could be challenging.

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.