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

Chemical Properties

Colorless liquid

Uses

Different sources of media describe the Uses of 996-50-9 differently. You can refer to the following data:
1. Trimethylsilyldiethylamine is a reagent used as an electrophilic trimethylsilyl source for cleavage of cyclic ethers, esters, oxazolidines, and cyclic acetals; also as a nucleophilic source of the diethylamino group, participating in the following synthesis reactions: Trimethylsilyl Group Transfer, Diethylamino Group Transfer, Trimethylsilyldiethylamine as Halosilane Equivalent, Silylation of Alcohols, Mild Generation of Phosphonochloridates, Silylation of Amines, Diethylamino Group Transfer, Conjugate Addition, Aminoalkylation of Aldehydes, Enamine and Silyl Enol Ether Preparation, Mediation of 1,4-Conjugate Additions, etc.
2. It is used to derivative polar organic compounds. N,N-Diethyl(trimethylsilyl)amine is a chemical reagent with wide application in organic chemistry and used in stereo specific addition reactions as well as in SN2 nucleophilic substitutions.

Definition

ChEBI: An N-silyl compound that is diethylamine in which the amino hydrogen is replaced by a trimethylsilyl group. N-(trimethylsilyl)diethylamine is a derivatisation agent used in gas chromatography/mass spectrometry applicat ons.

General Description

N,N-Diethyltrimethylsilylamine is a silylating agent used to derivatize polar organic 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

• 75-79-6 Methyltrichlorosilane 
• 5775-33-7 N-chlorodiethylamine 
• 2857-97-8 trimethylsilyl bromide 
• 21458-75-3 2-diethylamino-5,5-dimethyl-1,3,2-dioxaphosphorinane 
• 109-89-7 diethylamine 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 
• 660-68-4 diethyl amine hydrochloride 
• 102-53-4 bis-(diethylamino)methane 
• 153080-51-4 C₁₁H₂₇PS₄Si 
• 1118-02-1 trimethylsilyl isocyanate 
• 1608-26-0 Hexamethylphosphorous triamide 
• 7677-24-9 trimethylsilyl cyanide 
• 126989-46-6 N,N-Diethyl-S-isopropylsulfenamide 
• 127612-42-4 S,S-diisopropyl O-(trimethylsilyl) phosphorodithioite 

Downstream Products

• 18406-05-8 4-(trimethylsilanyl-amino)-benzoic acid trimethylsilanyl ester 
• 7364-46-7 N-trimethylsilanyl-L-leucine trimethylsilanyl ester 
• 2899-52-7 N,O-bis-(trimethylsilyl)phenylalanine 
• 1146-59-4 N,N-diethyl-N'-phenyl-N'-trimethylsilyl urea 
• 1053-53-8 N,N-Diethyl-N'-phenyl-N'--harnstoff 
• 15984-93-7 valine, N-trimethylsilyl-, trimethylsilyl ester 
• 1636-14-2 bis(diethylamino)phenylphosphine 
• 1636-15-3 (diethylamino)diphenylphosphine 
• 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 
• 7364-50-3 N,S-Bis-(trimethylsilyl)-cystein-trimethylsilylester 
• 7483-92-3 TMS-DL-Ile-OTMS 

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.