7688-51-9

Usage

Uses

Used in Organic Synthesis:
N-ALLYL-N N-BIS(TRIMETHYLSILYL)AMINE is used as a nucleophilic reagent for the preparation of complex bicyclic scaffolds by reacting with aryl aldehydes via imine formation followed by efficient multicomponent reactions. This application is crucial in the development of novel chemical compounds and structures with potential applications in various industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, N-ALLYL-N N-BIS(TRIMETHYLSILYL)AMINE is used as a reagent for the synthesis of Dithiasuccinoyl (Dts) heterocycle by reacting with bisthiocarbamoyl chloride. Dts heterocycle is an important intermediate in the development of new drugs and pharmaceutical compounds.
Used in Chemical Intermediates:
N-ALLYL-N N-BIS(TRIMETHYLSILYL)AMINE is used as a reagent for the preparation of allyl selenide by reacting with aryl selenium salt in the presence of a ruthenium catalyst. Allyl selenide is a key intermediate in organic synthesis, which can be further utilized in the development of various chemical products and materials.
Used in Hydrosilylation and Hydroboration Reactions:
N-ALLYL-N N-BIS(TRIMETHYLSILYL)AMINE is used as a reagent in hydrosilylation and hydroboration reactions, which are important processes in the synthesis of various organic compounds and materials.
Used in Electrochemistry:
In the field of electrochemistry, N-ALLYL-N N-BIS(TRIMETHYLSILYL)AMINE may be used as an electrolyte additive, enhancing the performance and efficiency of electrochemical systems and devices.

InChI:InChI=1/C9H23NSi2/c1-8-9-10(11(2,3)4)12(5,6)7/h8H,1,9H2,2-7H3

Upstream product

• 10519-97-8 allylamino-trimethyl-silane 
• 107-11-9 1-amino-2-propene 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 1070-89-9 sodium hexamethyldisilazane 
• 106-95-6 allyl bromide 
• 109-64-8 1,3-dibromo-propane 
• 75-77-4 chloro-trimethyl-silane 
• 107-05-1 3-chloroprop-1-ene 
• 4039-32-1 lithium hexamethyldisilazane 
• 40949-94-8 potassium hexamethylsilazane 
• 107-37-9 allyltrichlorosilane 
• 758-44-1 N-bromobis(trimethylsilyl)amine 
• 17898-21-4 triethylallylsilane 
• 2551-83-9 allyltrimethoxysilane 

Downstream Products

• 17864-20-9 1,1,1,3,3,3-hexamethyl-2-(3-phenylsilanyl-propyl)-disilazane 
• 132592-88-2 3-Azabicyclo<3.1.0>hexan-2-on 
• 82260-00-2 (+/-)-TAMP 
• 82259-99-2 cis-2-(Aminomethyl)-1-cyclopropancarbonaseure 
• 132592-83-7 (cis)-2-(Aminomethyl)-1-cyclopropancarbonsaeure-methylester-Hydrochlorid 
• 132592-84-8 (trans)-2-(Aminomethyl)-1-cyclopropancarbonsaeure-methylester-Hydrochlorid 
• 23764-31-0 N-propylpropane-1,3-diamine 
• 111-26-2 hexan-1-amine 
• 14370-82-2 allyl phenyl selenide 
• 107-46-0 Hexamethyldisiloxane 
• 10017-11-5 allylammonium chloride 
• 109-76-2 Trimethylenediamine 
• 156-87-6 propan-1-ol-3-amine 
• 957214-81-2 N-allyl-N-(1-(2-bromophenyl)-2-formylethyl)-acetamide 

Relevant academic research and scientific papers

Lithium and potassium bis(trimethylsilyl)amide: Utilizing non-nucleophilic bases as nitrogen sources

Lithium and potassium bis(trimethylsilyl)amides are successfully utilized as nitrogen sources in palladium(0) catalyzed aminations of allylchloride.

Anionic synthesis of primary amine functionalized polystyrenes via hydrosilation of allylamines with silyl hydride functionalized polystyrenes

A general anionic ω-chain-end functionalization methodology is described and illustrated by the synthesis of ω-primary amine functionalized polystyrenes. First, the quantitative ω-silyl hydride functionalization of well-defined poly(styryl)lithium (Mn = 2200 and 14 100 g/mol) was effected with dimethylchlorosilane in hydrocarbon solution at room temperature. In the second step, involving amination by hydrosilation, the silyl hydride functionalized polystyrene was added quantitatively to 3-[N,N-bis(trimethylsilylamino]-1-propene, a protected amine, using Karstedt's Pt(0) hydrosilation catalyst in benzene. One of the principal advantages of this method is the fact that it is not necessary to use protecting groups for many functional groups, as illustrated by the quantitative primary amine functionalization of ω-silyl hydride functionalized poly(styryl)lithium with allylamine using the Karstedt's hydrosilation catalyst. The silyl hydride and amine functionalized polystyrenes were characterized by SEC, FTIR, 1H and 13C NMR, MALDI-TOF mass spectrometry, and end-group titration.

Synthesis of bifunctional disiloxanes: Via subsequent hydrosilylation of alkenes and alkynes

The first protocol for the synthesis of unsymmetrical bifunctional 1,1,3,3-tetramethyldisiloxane derivatives via subsequent hydrosilylation of alkenes and alkynes is presented. The methodology described has vast functional group tolerance and is extremely efficient towards the formation of novel disiloxane-based building blocks.

Preparation of N, N-bis(trimethylsilyl)allylamine

The invention discloses a preparation method of N, N-bis(trimethylsilyl)allylamine, which comprises the following steps: 1. dropwisely adding an organic alkali solution into allyl bromide to carry outcondensation reaction, carrying out rotary evaporation to remove the organic solvent after the reaction is completed, and filtering to remove the generated metal salt, thereby obtaining a filtrate; and 2, adding deionized water into the filtrate, carrying out low-temperature water washing to remove metal salt and other water-soluble impurities, carrying out standing and liquid separation, separating out an organic phase, rectifying the organic phase, and collecting the N, N-bis(trimethylsilyl)allylamine finished product. The method has the advantages that 1, the reaction safety coefficient isgreatly improved, and the corrosion to equipment is effectively reduced; and 2, by-products or impurities generated in the preparation process are effectively removed, so that the purity and yield ofthe product are effectively improved.

METHOD FOR PRODUCING SILANE COMPOUND HAVING BIS-SILYLAMINO GROUP

PROBLEM TO BE SOLVED: To provide a method for producing a silane compound having a bis-silylamino group efficiently, stably, and in good yield. SOLUTION: A method for producing a silane compound having a bis-silylamino group represented by the formula (3) includes reacting a compound represented by the formula (2): HSiR8nX3-n (2) with a compound represented by the formula (1) in the presence of a platinum compound where the compound represented by the formula (1) having a content of a compound represented by the formula (4) of not greater than 5.0 mass% is used. In the formulae, R1 is a C1-18 bivalent hydrocarbon group, R1' is a C3-20 bivalent hydrocarbon group, R2-R8 and R9 are each independently a substituted or unsubstituted C1-20 monovalent hydrocarbon group, X is a halogen or OR9, and n is an integer of 0-2. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT

[...] group-containing organosilicon compound

[Problem] To provide a production method by which an organosilicon compound containing a bissilylamino group can be produced with high production efficiency and high yield through a simple and safe production process in which reaction control is easy. [Solution] A method for producing an organosilicon compound containing a bissilylamino group by subjecting an unsaturated hydrocarbon compound containing a bissilylamino group and an organosilicon compound containing a silicon-atom-bonded hydrogen atom to a hydrosilylation reaction in the presence of a hydrosilylation catalyst, the method being characterized in that the unsaturated hydrocarbon compound containing a bissilylamino group has a total content of a specific organosilicon compound and a specific amine compound of 0.2 mass% or less.

Discovery of (S)-3′-hydroxyblebbistatin and (S)-3′-aminoblebbistatin: polar myosin II inhibitors with superior research tool properties

In search of myosin II inhibitors with superior research tool properties, a chemical optimization campaign of the blebbistatin scaffold was conducted in this paper. (S)-Blebbistatin is the best known small-molecule inhibitor of myosin II ATPase activity. Unfortunately, as a research tool this compound has several deficiencies: it is photolabile and (photo)toxic, has low water solubility, and its (fluorescent) precipitates interfere in (fluorescence) readouts. In view of obtaining tool compounds with improved properties, both enantiomers of a series of D-ring modified polar analogs were prepared. We identified (S)-3′-hydroxyblebbistatin (S)-2 and (S)-3′-aminoblebbistatin (S)-3 as two myosin II inhibitors with a 30-fold higher water solubility than (S)-blebbistatin. These molecules furthermore do not cause interference in (fluorescence) readouts. (S)-2 and (S)-3 thus are superior alternatives to (S)-blebbistatin as research tools to study myosin II.

Synthesis of methyl(1-aminophosphonate)siloxane oligomers

A synthesis of 1-aminophosphonate derivative of methylsiloxane oligomer was developed. A methodology of the introduction of 1-aminophosphonate fragment not only into the stable siloxane structures, but also into hydrolytically unstable alkoxyfunctional organosilicon compounds was suggested.

Reaction of hexylsilane with N-substituted allylamine and allyl chloride

Reactions of allyldiethylamine and allylbis(trimethylsiyl)amine with hexylsilane are studied. The former reaction involves hydrogen evolution and Si-Si bond formation. The contribution of hydrosilylation is insignificant. Substituent exchange between the nitrogen and silicon atoms in the silane is found. In the reaction with allylbis(trimethylsilyl)amine, no evolution of hydrogen is observed, and hydrosilylation takes place. With allyl chloride, hydrosylilation, reduction, and Si-Si bond formation are observed. Quantumchemical calculations for the reactions with diethylallylamine and allylbis(trimethylsilyl)amine were carried out at the PM3, B3LYP/6-31G**, and B3LYP/LanL2DZ levels to show that these reactions all are thermodynamically allowed, and the difference in the behavior of the amines is explained by kinetic and conformational factors. Pleiades Publishing, Inc., 2006.

Spin chemistry of organometallic compounds. 2. Interaction of N-bromohexamethyldisilazane with allyltriorganolsilanes

Two instances have been considered demonstrating the influence of organoelement substituent on the reactivity of radicals generated from R3MCH2CH=CH2 (M = Si or Sn) in photoinduced interaction with (Me3Si)2