N,N-Dimethyltrimethylsilylamine

Base Information

• Chemical Name: N,N-Dimethyltrimethylsilylamine
• CAS No.: 2083-91-2
• Molecular Formula: C5H15NSi
• Molecular Weight: 117.266
• Hs Code.: 29319090
• European Community (EC) Number: 218-222-3
• UNII: R5D6N5EJ26
• DSSTox Substance ID: DTXSID7062168
• Nikkaji Number: J43.464G
• Wikidata: Q72472304
• Mol file: 2083-91-2.mol

Synonyms:N,N-Dimethyltrimethylsilylamine;2083-91-2;N,N-Dimethylaminotrimethylsilane;N-(Trimethylsilyl)dimethylamine;Pentamethylsilylamine;Silanamine, pentamethyl-;(Dimethylamino)trimethylsilane;TMSDMA;Silanamine, N,N,1,1,1-pentamethyl-;Dimethylaminotrimethylsilane;N-methyl-N-trimethylsilylmethanamine;N,N,1,1,1-pentamethylsilanamine;N,N-Dimethyltrimethylsilamine;Dimethylamine, TMS derivative;R5D6N5EJ26;(n,n-dimethylamino)trimethylsilane;MFCD00008297;TMS-DMA;trimethylsilyldimethylamine;Dimethyl(trimethylsilyl)amine;UNII-R5D6N5EJ26;Dimethylamino(trimethyl)silane;N-Trimethylsilyl-dimethylamine;SCHEMBL377532;Dimethyl-trimethylsilanyl-amine;(CH3)3SiN(CH3)2;n,n-dimethyl-trimethylsilylamine;DTXSID7062168;EINECS 218-222-3;CD5400;n,n-dimethyl-n-(trimethylsilyl)amine;N,N-Dimethyltrimethylsilylamine, 97%;AKOS006222984;FS-5233;N,N-DIMETHYL(TRIMETHYLSILYL)AMINE;T0591;S06925;N,N-Dimethyltrimethylsilylamine, Selectophore(TM);J-013669;N,N-Dimethyltrimethylsilylamine, purum, >=95.0% (GC)

Chemical Property of N,N-Dimethyltrimethylsilylamine

Chemical Property:

• Appearance/Colour: clear colorless to pale yellow liquid
• Vapor Pressure: 4.11mmHg at 25°C
• Melting Point: <0 °C
• Refractive Index: n20/D 1.397(lit.)
• Boiling Point: 89.3 °C at 760 mmHg
• PKA: 10.77±0.70(Predicted)
• Flash Point: -19 °C
• PSA: 3.24000
• Density: 0.761 g/cm³
• LogP: 1.38290
• Storage Temp.: Flammables area
• Sensitive.: Moisture Sensitive
• Water Solubility.: Decomposition
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 117.097376017
• Heavy Atom Count: 7
• Complexity: 53.6

Purity/Quality:

99.9% ^*data from raw suppliers

(N,N-Dimethylamino)trimethylsilane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F, C
• Hazard Codes: F,C
• Statements: 11-34
• Safety Statements: 16-26-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Metals -> Metalloid Compounds (Silicon)
• Canonical SMILES: CN(C)[Si](C)(C)C
• General Description: N,N-Dimethyltrimethylsilylamine (Me3SiNMe2) is a silylamine compound formed as the primary product in the reaction of iodo(trimethyl)silane (Me3SiI) with N,N-dimethylformamide (DMF) or N,N-dimethylacetamide (DMA), resulting from the cleavage of the N–C(=O) bond. It is accompanied by the generation of acyl iodides (RCOI) and minor by-products such as N-methyl-N-trimethylsilyl derivatives and N-methyl imides. The reaction proceeds via an intermediate quaternary ammonium salt, which decomposes to yield Me3SiNMe2 with high efficiency (83% for DMF and 77% for DMA).

Technology Process of N,N-Dimethyltrimethylsilylamine

There total 22 articles about N,N-Dimethyltrimethylsilylamine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

dimethyl amine (124-40-3) + 1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) → N,N-Dimethyltrimethylsilylamine (2083-91-2)

Guidance literature:

With 1,3-dimethyl-2-imidazolidinone; at 40 ℃; Reagent/catalyst;

Reference yield: 90.0%

trimethylsilyl <(dimethylamino)methyl>methylcarbamate (91749-17-6) → 1,3,5-trimethyl-1,3,5-triazacyclohexane (108-74-7) + N,N-Dimethyltrimethylsilylamine (2083-91-2)

Guidance literature:

at 20 ℃; for 360h; nitrogen atmosphere;

Reference yield: 83.0%

bis-(dimethylamino)methane (51-80-9) + bis(trimethylsilyl) 2-(2-furyl)ethylphosphonite (333364-16-2) → N,N-Dimethyltrimethylsilylamine (2083-91-2) + O-trimethylsilyl-[2-(2-furyl)ethyl](dimethylaminomethyl)phosphinate

Guidance literature:

With zinc(II) chloride; at 130 ℃; for 1h;

upstream raw materials:

chloro-trimethyl-silane

dimethyl amine

N-(trimethylsilylmethyl)methylamine

methyl-bis(dimethylamino)phosphine

Downstream raw materials:

trimethylsilyl fluoride

N,N-dimethyl(trimethylsilyl)acetamide

N-chloro-N-trimethylsilyl-4-toluenesulfonamide

sarcosine dimethylamide

Refernces

Reaction of iodo(trimethyl)silane with N,N-dimethyl carboxylic acid amides

10.1134/S1070428010060035

The study investigates the reactions of iodo(trimethyl)silane (Me3SiI) with N,N-dimethylformamide (DMF) and N,N-dimethylacetamide (DMA) at a molar ratio of 1:2. The primary outcome is the cleavage of the N–C(=O) bond, leading to the formation of N,N-dimethyltrimethylsilylamine (Me3SiNMe2) and the corresponding acyl iodides (RCOI, where R = H or Me). In the reaction with DMF, formyl iodide (HCOI) was detected for the first time using gas chromatography–mass spectrometry. The study also observed the formation of N-methyl-N-trimethylsilyl derivatives and N-methyl imides as by-products. The initial intermediate in these reactions is identified as a quaternary ammonium salt [Me2(Me3Si)N+COR]I–, which decomposes via dissociation of the N–CO and N–Me bonds. The overall yield of Me3SiNMe2 was 83% for R = H and 77% for R = Me.

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