13686-66-3

Basic information

• Product Name: DIMETHYLSILYLDIETHYLAMINE
• Synonyms: N,N-DIETHYL-1,1-DIMETHYLSILYLAMINE;DIETHYLAMINODIMETHYLSILANE;DIMETHYLSILYLDIETHYLAMINE;Silanamine,N,N-diethyl-1,1-dimethyl-;n,n-diethyl-1,1-dimethyl-silanamin;N,N-Diethyldimethylsilanamine;N,N-diethyl-1,1-dimethyl-Silanamine;N-dimethylsilyl-N-ethylethanamine
• CAS NO: 13686-66-3
• Molecular Formula: C₆H₁₇NSi
• Molecular Weight: 131.29
• EINECS: 237-202-5
• Product Categories: Organometallic Reagents;Organosilicon;Others;Chemical Synthesis;Organometallic Reagents
• Mol File: 13686-66-3.mol

Chemical Properties

• Boiling Point: 109 °C
• Flash Point: 24.6 °C
• Appearance: /
• Density: 0.8
• Refractive Index: 1.4080
• Solubility: sol common aprotic organic solvents.
• Sensitive: Moisture Sensitive
• BRN: 741862
• CAS DataBase Reference: DIMETHYLSILYLDIETHYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: DIMETHYLSILYLDIETHYLAMINE(13686-66-3)
• EPA Substance Registry System: DIMETHYLSILYLDIETHYLAMINE(13686-66-3)

Safety Data

• Hazard Codes: F,Xi
• Statements: 11-36/37/38
• Safety Statements: 16-23-26-36
• RIDADR: 1993
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 13686-66-3(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
DIMETHYLSILYLDIETHYLAMINE is used as a reagent for the conversion of hydroxy groups of allyl or homoallyl alcohols into hydrodimethylsilyl ethers. This conversion is particularly useful in intramolecular hydrosilation reactions, which are important in the synthesis of various organic compounds.
Used in Comparison to Other Reagents:
In some cases, DIMETHYLSILYLDIETHYLAMINE gives superior results compared to the more commonly employed 1,1,3,3-tetramethyldisilazane (TMDS). This makes it a valuable alternative for chemists looking to optimize their reaction conditions and improve the efficiency of their synthesis processes.
Physical Properties:
DIMETHYLSILYLDIETHYLAMINE has a boiling point of 112°C at 760 mmHg, a refractive index (n20 D) of 1.4087, and a density (d20 4) of 0.7505 g/cm3. These properties are important for understanding its behavior in various chemical reactions and for determining the appropriate conditions for its use in the laboratory.

Preparation

by treatment of commercially available chlorodimethylsilane (ClMe2SiH) and diethylamine in the presence of triethylamine in ether, followed by filtration and distillation.

InChI:InChI=1/C6H16NSi/c1-5-7(6-2)8(3)4/h5-6H2,1-4H3

Upstream product

• 109-89-7 diethylamine 
• 6026-02-4 (N,N-diethylamino)dimethylchlorosilane 
• 1066-35-9 dimethylmonochlorosilane 
• 4669-59-4 bis(diethylamino)dimethylsilane 

Downstream Products

• 57586-53-5 Dimethylsilanyl-{4-[4-(1,1,3,3-tetramethyl-disilazan-2-yl)-benzyl]-phenyl}-amine 
• 122214-22-6 {Dimethyl-[2-methylene-cyclohex-(Z)-ylidenemethyl]-silanyl}-diethyl-amine 
• 122214-23-7 {Dimethyl-[2-methylene-cyclohex-(E)-ylidenemethyl]-silanyl}-diethyl-amine 
• 41034-90-6 N-ethyl-N-(furan-2-ylmethyl)ethanamine 
• 34306-01-9 N-ethyl-N-(4-methylbenzyl)ethanamine 
• 24619-87-2 N-ethyl-N-(4-chlorobenzyl)ethanamine 
• 27959-08-6 N-ethyl-N-(4-nitrobenzyl)ethanamine 
• 772-54-3 N,N-diethylbenzylamine 
• 15429-16-0 N,N-diethyl-1-phenylethylamine 
• 69293-74-9 p-(diethylaminomethyl)benzonitrile 
• 27640-12-6 N,N-diethyl-benzenepropanamine 
• 519-72-2 diethyl-benzhydryl-amine 
• 100482-74-4 diethyl-(1-methyl-3-phenyl-propyl)-amine 
• 68453-55-4 methyl 4-((diethylamino)methyl)benzoate 

Relevant articles and documents

INSERTION OF DIMETHYLSILYLENE INTO O-H AND N-H SINGLE BONDS

Dimethylsilylene, generated by photolysis of dodecamethylcyclohexasilane, inserts efficiently into O-H single bonds of alcohols to yield alkoxydimethyl-silanes.Use of ethanol-O-d1 yields ethoxydimethylsilane-Si-d1.Dimethylsilylene also inserts into O-H single bonds of water or D2O to yield respectively tetramethyldisiloxane or tetramethyldisiloxane-Si2-d2.Dimethylsilylene also inserts into N-H bonds of primary and secondary amines to yield aminodimethylsilanes.This reaction provides an efficient route to difunctional silanes.

Lewis acid-catalyzed reductive amination of carbonyl compounds with aminohydrosilanes

The TiCl4-catalyzed reaction of aromatic carbonyl compounds with (dialkylamino)dimethylsilanes gave tertiary amines in moderate to high yields. The reductive amination of aliphatic aldehydes was effectively catalyzed by ZnI2. Methyl

A novel route to chlorodimethylsilane

A new efficient laboratory method of preparation of chlorodimethylsilane (Cl(CH3)2SiH) has been elaborated, which is a modification of the Eaborn et al. method (34) and is based on a transsilylation reaction of substituted (amino)dimethylhydrosilanes, R2NSiMe2H (R2 = Me2, Et2, (CH2)n, etc.) with dimethyldichlorosilane (Me2SiCl2). The reaction proceeds at reflux, at 70°C, preferably with an excess of Me2SiCl2. The most important feature of this novel method is a recovery of intermediate (amino)chlorodimethylsilanes (R2NSiMe2Cl), which can be again reduced to R2NSiMe2H. The transsilylation mechanism has been proven by reaction of (diethylamino)methylphenylsilane with Me2SiCl2. The products of this latter reaction are HMePhSiCl and R2NSiMe2Cl, thus a disproportionation mechanism has been excluded. New substituted bis(amino)dimethylsilanes ((R2N)2SiMe2), (amino)dimethylchlorosilanes (R2NSiMe2Cl), and (amino)dimethylhydrosilanes (R2NSiMe2H) have been synthesized and characterized by NMR and IR.