2097-16-7

Usage

Chemical Class

Silatranes

Composition

Silicon atom bonded to five carbon atoms and a nitrogen atom

Physical State

Colorless liquid

Odor

Faint

Applications

Research and industrial applications

Use as a Reagent

Chemical synthesis

Building Block

Production of other silicon-containing compounds

Thermal Stability

High

Nucleophilic Ability

Strong

Lewis Base

Acts as a Lewis base in organic reactions

Pharmaceutical Use

Manufacture of pharmaceuticals

Cross-linking Agent

Production of polymers and resins

Research Field

Organometallic catalysis

InChI:InChI=1/C8H17NO3Si/c1-2-13-10-6-3-9(4-7-11-13)5-8-12-13/h2-8H2,1H3

Upstream product

• 115-21-9 ethyltrichlorosilane 
• 102-71-6 triethanolamine 
• 20836-42-4 2,2',2''-tris(trimethylsiloxy)triethylamine 
• 627-44-1 diethylmercury 
• 33446-83-2 1-Iodosilatrane 
• 78-07-9 ethyltriethoxy silane 
• 283-60-3 silatrane 
• 92085-71-7 1-allyl-2,8,9-trioxa-5-aza-1-silabicyclo<3.3.3>undecane 
• 144967-56-6 2-ethyl-2-phenyl-6-<2-(trimethylsiloxy)ethyl>-1,3,6,2-dioxazasilocane 

Downstream Products

• 107-27-7 ethylmercury(II) chloride 
• 1219360-11-8 C₈H₁₉NO₄Si*C₉H₁₀O₃ 

Relevant academic research and scientific papers

Direct synthesis of 1-organylsilatranes from organyltrichlorosilanes and tris(2-hydroxyethyl)amine

A direct method of synthesis of 1-organylsilatranes by the reaction of organyltrichlorosilanes with tris(2-hydroxyethyl)amine was developed. 1-Organylsilatranes RSi(OCH2CH2)3N with R = Me, Et, Ph, ClCH2, ICH2, Cl(CH2)3 were prepared by this method in up to 72% yield.

MEDIUM-SIZED SILICON-CONTAINING RINGS. IV. SILOCANE-SILATRANE TRANSFORMATIONS

We have discovered an intramolecular condensation of trimethylsilyl ethers of silocines with a phenyl substituent on the silicon atom that leads to the corresponding silatranes.For the preparation of N-(hydroxyethy) derivatives of silocines we have, for the first time, used the cyclosilylation of triethanolamine with a bis(dialkylamino)silane.It was found that in the exothermic reaction of trialkoxyalkylsilanes with N-(hydroxyethyl) derivatives of silocines and their trimethylsilyl ethers the yield of silatranes is only slighthly dependent on the nature of the substituent both in the silocines and in the alkoxysilanes.

1-Halosilatranes

The electronic structure of 1-halosilatranes is discussed.Some new preparative methods based on hetero- and homo-lytic reactions of the silatrane and the Si- and C-substituted silatranes with halogenating reagents are described and also synthetic routes to 1-halosilatranes from certain organotrialkoxy- and organotrichlorosilanes.The electrophilic reactions of 1-iodosilatrane with ethers and esters, carbonyl compounds, alkoxysilanes and siloxanes, terminal alkynes and organomercurials have been studied

DIRECT TRANSFER OF ALIPHATIC AND AROMATIC SUBSTITUENTS FROM ORGANOSILATRANES TO MERCURY(II) SPECIES

The relative reaction rates of several silatranes (derivatives of 2,8,9-trioxa-5-aza-1-silatricyclo1,5>undecane) and HgCl2 in acetone-d6 to yield the corresponding organomercury compound are of the order of e.g., 5 * 10-1 1 mol-1 sec-1 or slightly less, a rate that is unexpectedly high compared to the essentially inert parent organotrialkoxysilanes.Thus, the apical Si-C bond of the silatrane is extraordinarily susceptible to direct electrophilic attack by mercury(II).The rates decrease in the order CH2=CH, C6H5, p-ClC6H4 > CH3 > CH3CH2, CH3CH2CH2 > C6H11, ClCH2, Cl2CH, CH3CH2O.The effects of varying the solvent and the counterions are noted, and the probable mechanism is discussed.