Vinyltrimethylsilane

• Catalog No.: L16989
• CAS Number: 754-05-2
• M. F.: C5H12Si
• M. W.: 100.23428
• Purity: 98+%

SYNONYMS

• Title: 乙烯基三甲基硅烷
• IUPAC name: ethenyltrimethylsilane
• IUPAC Traditional name: silane, ethenyltrimethyl-
• Synonyms: Trimethylvinylsilane

DATABASE IDS

• EC Number: 212-042-9
• MDL Number: MFCD00008606
• CAS Number: 754-05-2
• Beilstein Number: 956572

PROPERTIES

• Purity: 98+%
• Boiling Point: 54-56°C
• Density: 0.690
• Flash Point: -24°C(-11°F)
• Melting Point: -132°C
• Refractive Index: 1.3910
• GHS Hazard statements: H225-H315-H319-H335
• European Hazard Symbols: Irritant (Xi)
• European Hazard Symbols: Flammable (F)
• GHS Precautionary statements: P210-P280G-P243-P305+P351+P338-P403+P233
• Risk Statements: 11-36/37/38
• Safety Statements: 9-16-26-29-33-37
• TSCA Listed: 是
• Hazard Class: 3
• UN Number: UN1993
• Packing Group: II

REFERENCES

• 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 ?-carbon atom. See Appendix 4.
• Acylation under Friedel-Crafts conditions leads to vinyl ketones. Using ɑ?-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):
  
• For reviews of the Nazarov cyclization, see: Synthesis, 429 (1983); Org. React., 45, 159 (1994).
• 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).
• 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.
• For use in a 2-carbon extension of aldehydes to ɑ?-unsaturated aldehydes based on cycloaddition to the nitrone, see N-Methylhydroxylamine hydrochloride, L02202.
• For an extensive review of the reactions of vinyl (and allyl) silanes, see: Org. React., 37, 57 (1989).