Allyltrimethylsilane

• Catalog No.: A14662
• CAS Number: 762-72-1
• M. F.: C6H14Si
• M. W.: 114.26086
• Purity: 98+%

SYNONYMS

• Title: 烯丙基三甲基硅烷
• IUPAC name: trimethyl(prop-2-en-1-yl)silane
• IUPAC Traditional name: silane, trimethyl-2-propenyl-

DATABASE IDS

• EC Number: 212-104-5
• CAS Number: 762-72-1
• Beilstein Number: 906755
• MDL Number: MFCD00008635

PROPERTIES

• Purity: 98+%
• Boiling Point: 85-86°C
• Density: 0.717
• Flash Point: -10°C(14°F)
• Refractive Index: 1.4080
• GHS Hazard statements: H225-H315-H319-H335
• European Hazard Symbols: Irritant (Xi)
• European Hazard Symbols: Flammable (F)
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A
• Risk Statements: 11-36/37/38
• Safety Statements: 9-16-23-26-33-37
• TSCA Listed: 是
• Hazard Class: 3
• UN Number: UN1993
• Packing Group: II

REFERENCES

• Reactions with electrophiles illustrate the ?-effect (see Appendix 4); e.g. acid chlorides with a Lewis acid give allyl ketones: J. Organomet. Chem., 85, 149 (1975):
  
• Similarly, carbonyl compounds are converted to homoallylic alcohols: J. Organomet. Chem., 69, C15 (1974). In the TiCl₄ promoted reaction with enones, behaves as an allyl anion equivalent, giving the product of conjugate addition (Hosomi-Sakurai reaction): J. Am. Chem. Soc., 99, 1673 (1977);105, 2354 (1983); Org. Synth. Coll., 7, 443 (1990):
  
• More recent studies have shown that TMS cyclopentanes are also formed in these reactions via a competing [3+2] cycloaddition mechanism: Tetrahedron, 49, 9955 (1993). Chemoselective addition to aldehydes can be accomplished in the presence of a ketone, using Scandium(III) trifluoromethanesulfonate hydrate, 40566 as catalyst: Synthesis, 1822 (1998).
• In the presence of F^-, functions as an allyl anion equivalent, affording homoallylic alcohols from carbonyl compounds: Tetrahedron Lett., 3043 (1978), and adding to a variety of Michael acceptors: Tetrahedron Lett., 25, 3213 (1984); J. Org. Chem., 51, 1745 (1986). For a review of reactivity in the presence of Lewis acids and F^-, see: J. Prakt. Chem./ Chem. Ztg., 336, 375 (1994).
• Has also been used, in the presence of a catalyst such as p-TsOH, I₂, Br₂ or TfOH, as a silylating agent for alcohols, phenols and carboxylic acids: Tetrahedron Lett., 21, 835 (1980); J. Org. Chem., 46, 5212 (1981). The advantage over more conventional silylation methods is that the only by-product is the neutral gas propene.