996-50-9

Basic information

• Product Name: N,N-Diethyl-1,1,1-trimethylsilylamine
• Synonyms: DIETHYLAMINOTRIMETHYLSILANE;N,N-DIETHYLAMINOTRIMETHYLSILANE;N,N-DIETHYLTRIMETHYLSILYLAMINE;N,N-DIETHYL-1,1,1-TRIMETHYLSILYLAMINE;N-(TRIMETHYLSILYL)DIETHYLAMINE;TRIMETHYLSILYLDIETHYLAMINE;TRIMETHYL-N,N-DIETHYLAMINOSILANE;TMSDEA
• CAS NO: 996-50-9
• Molecular Formula: C₇H₁₉NSi
• Molecular Weight: 145.32
• EINECS: 213-637-6
• Product Categories: Aminosilanes;Analytical Chemistry;GC Derivatizing Reagents;Si (Classes of Silicon Compounds);Silicon Compounds (for Synthesis);Silylation (GC Derivatizing Reagents);Si-N Compounds;Synthetic Organic Chemistry;Trimethylsilylation (GC Derivatizing Reagents);Building Blocks;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks;Protected Amines;Halogenated Heterocycles
• Mol File: 996-50-9.mol
• Article Data: 27

Chemical Properties

• Melting Point: -10°C
• Boiling Point: 125-126 °C(lit.)
• Flash Point: 50 °F
• Appearance: clorless liquid
• Density: 0.767 g/mL at 25 °C(lit.)
• Vapor Density: >1 (vs air)
• Vapor Pressure: 14.2mmHg at 25°C
• Refractive Index: n20/D 1.411(lit.)
• Storage Temp.: Store at RT.
• PKA: 11.27±0.70(Predicted)
• Water Solubility: decomposes
• Sensitive: Moisture Sensitive
• BRN: 635718
• CAS DataBase Reference: N,N-Diethyl-1,1,1-trimethylsilylamine(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-Diethyl-1,1,1-trimethylsilylamine(996-50-9)
• EPA Substance Registry System: N,N-Diethyl-1,1,1-trimethylsilylamine(996-50-9)

Safety Data

• Hazard Codes: F,C
• Statements: 11-34
• Safety Statements: 26-36/37/39-45-24/25-16
• RIDADR: UN 2733 3/PG 2
• WGK Germany: 3
• F: 10-21
• TSCA: Yes
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 996-50-9(Hazardous Substances Data)

Usage

Description

N,N-Diethyl-1,1,1-trimethylsilylamine, also known as N,N-Diethyl(trimethylsilyl)amine, is a colorless liquid that serves as a versatile silylating agent in organic chemistry. It is an N-silyl compound derived from diethylamine, where the amino hydrogen is replaced by a trimethylsilyl group. This unique structure allows it to act as both an electrophilic trimethylsilyl source and a nucleophilic source of the diethylamino group, making it a valuable reagent in various synthesis reactions and applications.

Uses

Used in Organic Chemistry:
N,N-Diethyl-1,1,1-trimethylsilylamine is used as a reagent for the cleavage of cyclic ethers, esters, oxazolidines, and cyclic acetals. It is also employed in stereo-specific addition reactions and SN2 nucleophilic substitutions due to its ability to derivatize polar organic compounds.
Used in Trimethylsilyl Group Transfer:
As a trimethylsilyl group donor, N,N-Diethyl-1,1,1-trimethylsilylamine is used in Trimethylsilyl Group Transfer reactions, which are crucial for the protection of functional groups and the synthesis of various organic compounds.
Used in Diethylamino Group Transfer:
The diethylamino group in N,N-Diethyl-1,1,1-trimethylsilylamine can be transferred to other molecules, making it a useful reagent in Diethylamino Group Transfer reactions for the synthesis of a wide range of organic compounds.
Used in Silylation of Alcohols and Amines:
N,N-Diethyl-1,1,1-trimethylsilylamine is used for the silylation of alcohols and amines, which is an essential step in protecting these functional groups during organic synthesis and improving their stability.
Used in Mild Generation of Phosphonochloridates:
This reagent is employed in the mild generation of phosphonochloridates, which are important intermediates in the synthesis of various phosphorus-containing compounds.
Used in Enamine and Silyl Enol Ether Preparation:
N,N-Diethyl-1,1,1-trimethylsilylamine is utilized in the preparation of enamines and silyl enol ethers, which are key intermediates in organic synthesis and can participate in a variety of reactions.
Used in Mediation of 1,4-Conjugate Additions:
As a mediator, N,N-Diethyl-1,1,1-trimethylsilylamine facilitates 1,4-conjugate additions, which are important reactions in the synthesis of complex organic molecules.
Used in Gas Chromatography/Mass Spectrometry Applications:
N,N-Diethyl-1,1,1-trimethylsilylamine serves as a derivatization agent in gas chromatography/mass spectrometry applications, enhancing the detection and analysis of various compounds.

Purification Methods

Fractionate it through a 2ft vacuum-jacketed column containing Helipak packing with a reflux ratio of 10:1. [Sauer & Hasek J Am Chem Soc 68 241 1946, Langer et al. J Org Chem 23 50 1958, Rühlmann J Prakt Chem 9 315 1959, Beilstein 4 IV 4010.]

InChI:InChI=1/C7H19NSi/c1-6-8(7-2)9(3,4)5/h6-7H2,1-5H3

Upstream product

• 32833-97-9 N,N,S-triethyl-thiohydroxylamine 
• 118467-50-8 S,S-diethyl O-(trimethylsilyl) phosphorodithioite 
• 127612-42-4 S,S-diisopropyl O-(trimethylsilyl) phosphorodithioite 
• 126989-46-6 N,N-Diethyl-S-isopropylsulfenamide 
• 7677-24-9 trimethylsilyl cyanide 
• 109-89-7 diethylamine 
• 2857-97-8 trimethylsilyl bromide 
• 21458-75-3 2-diethylamino-5,5-dimethyl-1,3,2-dioxaphosphorinane 
• 102-53-4 bis-(diethylamino)methane 
• 153080-51-4 C₁₁H₂₇PS₄Si 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 
• 660-68-4 diethyl amine hydrochloride 
• 5775-33-7 N-chlorodiethylamine 
• 1118-02-1 trimethylsilyl isocyanate 

Downstream Products

• 7364-46-7 N-trimethylsilanyl-L-leucine trimethylsilanyl ester 
• 2899-52-7 N,O-bis-(trimethylsilyl)phenylalanine 
• 20841-05-8 N--hexamethyldisilazan 
• 15984-93-7 valine, N-trimethylsilyl-, trimethylsilyl ester 
• 20494-20-6 O-Phenyl-N-trimethylsilyl-N',N'-diethyl-isoharnstoff 
• 1636-14-2 bis(diethylamino)phenylphosphine 
• 20494-25-1 O-<2-Methoxy-phenyl)-N-trimethylsilyl-N',N'-diethyl-isoharnstoff 
• 1636-15-3 (diethylamino)diphenylphosphine 
• 7415-19-2 N_.O¹.O⁴-Tris(trimethylsilyl)-tyrosin 
• 18135-14-3 dimethyl trimethylsilyl phosphite 
• 4147-89-1 1,1,1-trimethyl-N-phenyl-N-(trimethylsilyl)-silanamine 
• 2078-24-2 hippuric acid trimethylsilanyl ester 
• 18881-57-7 trimethylsilyl diethyldithiocarbamate 
• 64625-17-8 N,O-di(trimethylsilyl)serine trimethylsilyl esther 

Relevant articles and documents

Lewis acid mediated, mild C-H aminoalkylation of azolesviathree component coupling

This manuscript reports the development of a mild, highly functional group tolerant and metal-free C-H aminoalkylation of azolesviaa three-component coupling approach. This method enables the C-H functionalization of diverse azole substrates, such as oxazoles, benzoxazoles, thiazoles, benzothiazoles, imidazoles, and benzimidazoles. DFT calculations identify a key deprotonation equilibrium in the mechanism of the reaction. Using DFT as a predictive tool, the C-H aminoalkylation of initially unreactive substrates (imidazoles/benzimidazoles) can be enabled through anin situprotecting/activating group strategy. The DFT-supported mechanistic pathway proposes key interactions between the azole substrate and the Lewis acid/base pair TBSOTf/EtNiPr2that lead to azole activation by deprotonation, followed by C-C bond formation between a carbene intermediate and an iminium electrophile. Two diverse approaches are demonstrated to explore the amine substrate scope: (i) a DFT-guided predictive analysis of amine components that relates reactivity to distortion of the iminium intermediates in the computed transition state structures; and (ii) a parallel medicinal chemistry workflow enabling synthesis and isolation of several diversified products at the same time. Overall, the presented work enables a metal-free approach to azole C-H functionalizationviaLewis acid mediated azole C-H deprotonation, demonstrating the potential of a readily available, Si-based Lewis acid to mediate new C-C bond formations.

Insertion of phenyl isocyanate into monoand diaminosilanes

The aminosilanes MenSi(NRR')4-n (n = 2,3) with NRR' = ethylamino (NHEt), n-propylamino (NHnPr), sec-butylamino (NHsBu), n-octylamino (NHnOct), n-dodecylamino (NHnDodec), allylamino (NHAll), tert-butylamino (NHtBu), diethylamino (NEt2), and anilino (NHPh) were synthesized and their reactions with phenyl isocyanate were studied. In all cases of these silanes Me3SiNRR' and Me2Si(NRR')2 formal insertion of the -NCO group into their Si-N bonds was observed, i.e. formation of products with Si-N (rather than Si-O) bonds was found. In some cases, the products could be crystallized and their molecular structures have been elucidated with single-crystal X-ray diffraction analyses.

Three-component coupling using arynes and aminosilanes for ortho-selective double functionalization of aromatic skeletons

(Chemical Equation Presented) Arynes were found to couple with aminosilanes and carbonyl compounds in the presence of benzoic acid to provide 2-aminobenzhydrols. Sulfonylimines could also be applied to the reaction, enabling amino and aminomethyl moieties to be incorporated into contiguous positions of aromatic skeletons. Only a small amount of the three-component coupling product was obtained in the absence of benzoic acid, which confirms its vital role in the present reaction.