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

L16989 Vinyltrimethylsilane, 98+%

CAS Number
754-05-2
Synonyms
Trimethylvinylsilane

Size Price ($) Quantity Availability
5g 43.67
25g 115.20
100g 370.80
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Vinyltrimethylsilane, 98+%

MDL
MFCD00008606
EINECS
212-042-9

Chemical Properties

Formula
C5H12Si
Formula Weight
100.24
Melting point
-132°
Boiling Point
54-56°
Flash Point
-24°(-11°F)
Density
0.690
Refractive Index
1.3910

Literature 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 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 Hazard and Precautionary Statements

Hazard Statements: H225-H315-H319-H335

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

Precautionary Statements: 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.

Other References

Beilstein
956572
Hazard Class
3
Packing Group
II
Harmonized Tariff Code
2931.90
TSCA
Yes

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