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

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

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

• 75-77-4 chloro-trimethyl-silane 
• 109-89-7 diethylamine 
• 75-79-6 Methyltrichlorosilane 
• 5775-33-7 N-chlorodiethylamine 
• 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 
• 1118-02-1 trimethylsilyl isocyanate 
• 1608-26-0 Hexamethylphosphorous triamide 
• 2857-97-8 trimethylsilyl bromide 
• 21458-75-3 2-diethylamino-5,5-dimethyl-1,3,2-dioxaphosphorinane 
• 102-53-4 bis-(diethylamino)methane 

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 
• 69859-22-9 (CH₃CH₂)2NCSN(C₆H₅)Si(CH₃)3 
• 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 

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.

An Alumino-Mannich Reaction of Organoaluminum Reagents, Silylated Amines, and Aldehydes

A multi-component coupling using organoaluminum reagents, silylated amines, and aldehydes results in the formation of tertiary amines. Both alkenyl- and alkylaluminum reagents undergo reaction with iminium ion substrates for which the corresponding Petasis borono-Mannich reactions are unsuccessful.

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.

Nucleophilic bromodifluoromethylation of iminium ions

A method for bromodifluoromethylation of iminium ions using Me3SiCF2Br is described. The reaction involves room temperature activation of the silicon reagent by HMPA to generate difluorocarbene, which upon interacting with excess of bromide ion provides bromodifluoromethyl carbanionic species. The iminium electrophiles are generated in situ from aldehydes, secondary amines, proton sponge, and silyl triflate. The reaction can be extended for introduction of chlorodifluoromethyl and iododifluoromethyl groups.

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.

Three-component coupling of arynes, aminosilanes, and aldehydes

A three-component coupling of arynes, aminosilanes, and aldehydes enables diverse amino and hydroxymethyl groups to be incorporated directly into 1,2-positions of aromatic rings.

Kinetics and mechanisms of silylation reactions: I. Catalytic alcoholysis and phenolysis of trimethylsilanes

Solvolysis of trimethyl(4-nitrophenoxy)silane and diethylamino(trimethyl)silane in 2-propanol, catalyzed by 4-nitrophenol and diethylamine, follows a scheme including 16 concurrent and consecutive reactions with participation of trimethylsilyl cation. Quantitative analysis of different reaction pathways shows that the main factor determining the predominant transformation pathways is specific solvation.

Novel method for preparing bis(trimethylsilyl) amines via treatment with trimethylsilylamines and methyl iodide

A convenient method for the synthesis of N,N-bis(trimethylsilyl)alkylamines has been reported. N-(Trimethylsilyl)diethylamine incorporated with a stoichiometric amount of methyl iodide was effective to convert primary amines, especially aromatic amines, and their monotrimethylsilyl derivatives into the corresponding N,N-bis(trimethylsilyl)amine derivatives in high yields. In the case of N-trimethylsilyl derivatives of aliphatic primary amines, a half-amount of silylamines served as a silylation agent against another half-amount of silylamines in the presence of 0.5 equivalent of methyl iodide to give N,N-bis(trimethylsilyl)alkylamines in good yield. Allyl iodide, allyl bromide and benzyl bromide were also effective to promote the silylation activity of silylamines.

Simple acid-base hydrolytic chemistry approach to new materials for second-order non-linear optics

Acid-base hydrolysis of aminqsilanes with NLO-active chromophores containing terminal acidic protons provides a facile synthetic route to robust dimeric, polymeric and molecularly self-assembled thin-film materials for second-order non-linear optics.

A Convenient Molecular Self-assembly Route to Thin Films containing Terminal Donor Ligands and Anchored Organotransition-metal Complexes for Heterogenized Homogeneous Catalysis

Simple acid-base hydrolytic chemistry on the surfaces of glass, quartz or silicon provides an easy access to thin films containing terminal amine and phosphine donor ligands which covalently bind a variety of organometallic complexes, and such oriented ultrathin films supporting a densely packed nickel(0) organometallic complex on glass, catalyse oligomerization of phenylacetylene.