13686-66-3 Usage
Description
DIMETHYLSILYLDIETHYLAMINE, also known as N,N-Diethylaminodimethylsilane, is an organic compound with the chemical formula (C2H5)2N(SiH(CH3)2). It is a colorless liquid with a characteristic amine-like odor. It is known for its reactivity and is commonly used in chemical synthesis and as a reagent in various applications.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 13686-66-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,3,6,8 and 6 respectively; the second part has 2 digits, 6 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 13686-66:
(7*1)+(6*3)+(5*6)+(4*8)+(3*6)+(2*6)+(1*6)=123
123 % 10 = 3
So 13686-66-3 is a valid CAS Registry Number.
InChI:InChI=1/C6H16NSi/c1-5-7(6-2)8(3)4/h5-6H2,1-4H3
13686-66-3Relevant articles and documents
INSERTION OF DIMETHYLSILYLENE INTO O-H AND N-H SINGLE BONDS
Gu, Tai-Yin Yang,Weber, William P.
, p. 7 - 11 (1980)
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.
A novel route to chlorodimethylsilane
Chrusciel
, p. 1405 - 1411 (2007/10/03)
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.