16087-24-4

Basic information

• Product Name: 1-Dimethylamino-4-trimethylsilylbenzene
• Synonyms: 1-Dimethylamino-4-trimethylsilylbenzene;BenzenaMine, N,N-diMethyl-4-(triMethylsilyl)-;N,N-DIMETHYL-4-(TRIMETHYLSILYL)ANILINE
• CAS NO: 16087-24-4
• Molecular Formula: C₁₁H₁₉NSi
• Molecular Weight: 193.36
• Mol File: 16087-24-4.mol
• Article Data: 9

Chemical Properties

• Melting Point: 27-28 °C
• Boiling Point: 253.7°Cat760mmHg
• Flash Point: 107.2°C
• Appearance: /
• Density: 0.9g/cm³
• Vapor Pressure: 0.018mmHg at 25°C
• Refractive Index: 1.495
• PKA: 4.57±0.12(Predicted)
• CAS DataBase Reference: 1-Dimethylamino-4-trimethylsilylbenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Dimethylamino-4-trimethylsilylbenzene(16087-24-4)
• EPA Substance Registry System: 1-Dimethylamino-4-trimethylsilylbenzene(16087-24-4)

Safety Data

• Hazardous Substances Data: 16087-24-4(Hazardous Substances Data)

Usage

Structure

A benzene ring with a dimethylamino (N(CH3)2) group at the 1-position and a trimethylsilyl (Si(CH3)3) group at the 4-position

Physical State

Colorless liquid at room temperature

Odor

Mild

Usage

Reagent in organic synthesis, particularly in the formation of silicon-carbon bonds

Applications

Building block in the production of pharmaceuticals and agrochemicals, precursor in the preparation of functionalized silicon materials for industrial applications

Reactivity

Unique reactivity and ability to introduce silicon atoms into organic molecules

Safety

Handle with care, follow proper safety protocols for chemical handling and storage

InChI:InChI=1/C11H19NSi/c1-12(2)10-6-8-11(9-7-10)13(3,4)5/h6-9H,1-5H3

Upstream product

• 1450-14-2 1,1,1,2,2,2-hexamethyldisilane 
• 1197-19-9 4-cyano-N,N-dimethylaniline 
• 586-77-6 4-bromo-N,N-dimethylaniline 
• 99-98-9 4-amino-N,N-dimethylaniline 
• 75-77-4 chloro-trimethyl-silane 
• 13190-50-6 4-dimethylaminophenyllithium 
• 121-69-7 N,N-dimethyl-aniline 
• 698-70-4 4-Iodo-N,N-dimethylaniline 
• 1112-54-5 vinyltriethylsilane 
• 153014-93-8 FpSiMe₂C₆H₄-p-NMe₂ 

Downstream Products

• 57650-42-7 tricarbonyl[5-(4-dimethylaminophenyl)cyclohexa-1,3-diene]iron 
• 1186026-67-4 1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-(trimethylsilyl)benzene 
• 76-86-8 Triphenylsilyl chloride 
• 121-69-7 N,N-dimethyl-aniline 
• 18036-96-9 trimethyl-(4-trimethylsilanyl-phenyl)-ammonium; iodide 

Relevant articles and documents

Rh(I)-catalyzed silylation of aryl and alkenyl cyanides involving the cleavage of C-C and Si-Si bonds

The Rh(I)-catalyzed silylation of nitriles with disilanes is described. The cleavage of inert carbon-cyano and silicon-silicon bonds occurs in this catalysis. Copyright

Design, Synthesis, and Implementation of Sodium Silylsilanolates as Silyl Transfer Reagents

There is an increasing demand for facile delivery of silyl groups onto organic bioactive molecules. One of the common methods of silylation via a transition-metal-catalyzed coupling reaction employs hydrosilane, disilane, and silylborane as major silicon sources. However, the labile nature of the reagents or harsh reaction conditions sometimes render them inadequate for the purpose. Thus, a more versatile alternative source of silyl groups has been desired. We hereby report a design, synthesis, and implementation of storable sodium silylsilanolates that can be used for the silylation of aryl halides and pseudohalides in the presence of a palladium catalyst. The developed method allows a late-stage functionalization of polyfunctionalized compounds with a variety of silyl groups. Mechanistic studies indicate that (1) a nucleophilic silanolate attacks a palladium center to afford a silylsilanolate-coordinated arylpalladium intermediate and (2) a polymeric cluster of silanolate species assists in the intramolecular migration of silyl groups, which would promote an efficient transmetalation.

P-Iodinations in hydrocarbon media: Continuous flow reactor application

Regiospecific iodination of aryl amines, that is, aryl compounds possessing strong electron donating groups (EDG's) in the p-position, is described. This procedure features not only the unique use of hydrocarbon media for such substitutions but also the absence of any oxidants aside from iodine itself. Further potential of this hydrocarbon media based electrophilic aromatic substitution is demonstrated by the coupling of the iodination with an in situ halogen/lithium exchange and product forming nucleophilic addition in a batch process. The protocol was ultimately scaled to a continuous flow reactor using an isolated p-iodoarylamine. Constituted as described, these procedures possess enhanced atom-economical, green and safety aspects compared to existing literature protocols.