2097-18-9

Basic information

• Product Name: 1-VINYLSILATRANE
• Synonyms: 9-trioxa-5-aza-1-silabicyclo(3.3.3)undecane,1-ethenyl-8;9-trioxa-5-aza-1-silabicyclo(3.3.3)undecane,1-vinyl-8;9-trioxa-5-aza-1-silabicyclo[3.3.3]undecane,1-ethenyl-8;Vinylsilatran;1-VINYLSILATRANE;VINYLSILATRANE;1-ethenylsilatrane;1-Vinyl-2,8,9-trioxa-5-aza-1-silabicyclo(3.3.3)undecane
• CAS NO: 2097-18-9
• Molecular Formula: C₈H₁₅NO₃Si
• Molecular Weight: 201.3
• EINECS: 218-262-1
• Mol File: 2097-18-9.mol
• Article Data: 4

Chemical Properties

• Melting Point: 163 °C
• Boiling Point: >110°C
• Flash Point: >110°C
• Appearance: /
• Density: 1.11 g/cm³
• CAS DataBase Reference: 1-VINYLSILATRANE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-VINYLSILATRANE(2097-18-9)
• EPA Substance Registry System: 1-VINYLSILATRANE(2097-18-9)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• TSCA: Yes
• Hazardous Substances Data: 2097-18-9(Hazardous Substances Data)

Usage

General Description

1-Vinylsilatrane is a chemical compound with the formula C4H9NOSi, often used in organic synthesis. Its chemical structure includes a five-membered heterocycle with nitrogen, silicon, and oxygen atoms. 1-VINYLSILATRANE is often utilized as a versatile synthetic building block due to its ability to undergo various chemical transformations. It is also known for its reactivity and can be used in different types of chemical reactions, such as hydrofunctionalization of alkenes, preparation of organosilanes, and cycloadditions. It's typically handled under controlled conditions due to its instability, requiring a comprehensive understanding of its properties for safe usage.

InChI:InChI=1/C8H15NO3Si/c1-2-13-9(3-6-10-13,4-7-11-13)5-8-12-13/h2H,1,3-8H2

Upstream product

• 78-08-0 Triethoxyvinylsilane 
• 283-56-7 2,8,9-trioxa-5-aza-1-borabicyclo[3.3.3]undecane 
• 102-71-6 triethanolamine 
• 144967-57-7 2-Phenyl-6-(2-trimethylsilanyloxy-ethyl)-2-vinyl-[1,3,6,2]dioxazasilocane 
• 75-94-5 trichlorovinylsilane 
• 20836-42-4 2,2',2''-tris(trimethylsiloxy)triethylamine 
• 2768-02-7 (vinyl)trimethoxylsilane 
• 144967-54-4 2-methyl-2-phenyl-6-<2-(trimethylsiloxy)ethyl>-1,3,6,2-dioxazasilocane 
• 118162-84-8 2-methyl-2-vinyl-6-(2-hydroxyethyl)-1,3,6,2-dioxazasilocane 
• 42959-18-2 2,2-dimethyl-6-(2-hydroxyethyl)-1,3,6,2-dioxazasilocane 

Downstream Products

• 126383-37-7 4-Chloro-N-[2-chloro-2-(2,8,9-trioxa-5-aza-1-sila-bicyclo[3.3.3]undec-1-yl)-ethyl]-benzenesulfonamide 
• 126383-39-9 N-[2-Chloro-2-(2,8,9-trioxa-5-aza-1-sila-bicyclo[3.3.3]undec-1-yl)-ethyl]-4-methyl-benzenesulfonamide 
• 102-71-6 triethanolamine 
• 143-48-6 Vinylsilantriol 
• 135587-16-5 1-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10-Hexadecafluoro-1-iodo-decyl)-2,8,9-trioxa-5-aza-1-sila-bicyclo[3.3.3]undecane 
• 135587-14-3 1-(3,3,4,4,5,5,6,6,7,7,8,8-Dodecafluoro-1-iodo-octyl)-2,8,9-trioxa-5-aza-1-sila-bicyclo[3.3.3]undecane 
• 126383-34-4 4-Chloro-N,N-bis-[2-chloro-2-(2,8,9-trioxa-5-aza-1-sila-bicyclo[3.3.3]undec-1-yl)-ethyl]-benzenesulfonamide 
• 126383-30-0 C₁₄H₁₉Cl₃N₂O₅SSi 
• 135587-15-4 1-(3,3,4,4,5,5,6,6,7,7,8,8,8-Tridecafluoro-1-iodo-octyl)-2,8,9-trioxa-5-aza-1-sila-bicyclo[3.3.3]undecane 
• 135587-13-2 1-(3,3,4,4,5,5,6,6,6-Nonafluoro-1-iodo-hexyl)-2,8,9-trioxa-5-aza-1-sila-bicyclo[3.3.3]undecane 
• 135587-12-1 1-(3,3,4,4,5,5,6,6-Octafluoro-1-iodo-hexyl)-2,8,9-trioxa-5-aza-1-sila-bicyclo[3.3.3]undecane 
• 112330-85-5 1-(2-perfluoropropyl-1-iodoethyl)silatrane 
• 135587-17-6 1-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-Heptadecafluoro-1-iodo-decyl)-2,8,9-trioxa-5-aza-1-sila-bicyclo[3.3.3]undecane 
• 126426-32-2 N,N-Bis(2-silatranyl-2-chloroethyl)benzenesulfonamide 

Relevant articles and documents

A novel route to pentacoordinated organylsilanes and -germanes

New convenient methods of sila- and germatranes synthesis from ethoxy- and tetraorganylsilanes and -germanes have been elaborated. The reaction of ethoxysilanes with boratrane in the presence of catalytic amounts of metal alcoholates has been investigated. Dimethylformamide (DMF) as a solvent and NaOEt as a catalyst used instead of xylene and Al(Oi-Pr)3 were found to give better yields. The possibility of using alkoxy-, aminosilanes, tetraethoxygermane and even tetraorganylsilanes in this reaction leading to the corresponding atranes with good yields has been demonstrated. Triethanolamine in the presence of catalytic amounts of base or CsF easily substitutes furyl-, dihydrofuryl-, dihydropyranyl- and thienyl groups in tris- and tetraheterylsilanes, leading to organylsilatranes with good to excellent yields.

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.