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754-05-2 - Vinyltrimethylsilane, 98+% - Trimethylvinylsilane - L16989 - Alfa Aesar

L16989 Vinyltrimethylsilane, 98+%

CAS-Nummer
754-05-2
Synonyme
Trimethylvinylsilane

Größe Preis ($) Menge Verfügbarkeit
5g 43,70
25g 132,00
100g 371,00
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Vinyltrimethylsilane, 98+%

MDL
MFCD00008606
EINECS
212-042-9

Chemische Eigenschaften

Formel
C5H12Si
Molmasse
100.24
Schmelzpunkt
-132°
Siedepunkt
54-56°
Flammpunkt
-24°(-11°F)
Dichte
0.690
Brechungsindex
1.3910

Literaturverweise

Useful ethylene equivalent in its reaction with electrophiles. The reactivity is controlled by the ability of the Si atom to stabilize a positive charge on a ß-carbon atom. See Appendix 4.

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Acylation under Friedel-Crafts conditions leads to vinyl ketones. Using ɑß-unsaturated acyl halides, the products are divinyl ketones, which, under the reaction conditions, undergo the Nazarov cyclization to enones: J. Org. Chem., 45, 1046 (1980):

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For reviews of the Nazarov cyclization, see: Synthesis, 429 (1983); Org. React., 45, 159 (1994).

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Coupling with the electrophilic reagent generated from an aryl iodide in the presence of Pd(OAc)2, triphenylphosphine and base, provides a route to styrenes: Chem. Lett., 1993 (1982).

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Also undergoes regioselective addition reactions with alkyllithiums: J. Chem. Soc., Perkin 1, 1131 (1983), and Grignards: Chem. Ber., 117, 383 (1984), to giveɑ-metallated products.

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For use in a 2-carbon extension of aldehydes to ɑß-unsaturated aldehydes based on cycloaddition to the nitrone, see N-Methyl­hydroxyl­amine hydrochloride, L02202.

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For an extensive review of the reactions of vinyl (and allyl) silanes, see: Org. React., 37, 57 (1989).

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GHS Gefahren- und Sicherheitshinweise

Gefahrenhinweise (EU): H225-H315-H319-H335

Highly flammable liquid and vapour. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Sicherheitshinweise: P210-P280g-P243-P305+P351+P338-P403+P233

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Wear protective gloves. Take precautionary measures against static discharge. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store in a well-ventilated place. Keep container tightly closed.

Weitere Referenzen

Beilstein
956572
Gefahrenklasse
3
Verpackungsgruppe
II
Harmonized Tariff Code
2931.90
TSCA
Yes

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