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A14662
Allyltrimethylsilane, 98+%

CAS: 762-72-1 MDL: MFCD00008635  EINECS: 212-104-5
UN#:UN1993Hazard Class:3Packing Group:II

 

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Chemical Properties

Formula: CH2=CHCH2Si(CH3)3  Flash point: -10°(14°F)
Formula weight: 114.27  Density: 0.717
Boiling point: 85-86° Refractive Index: 1.4080

Literature References

Reactions with electrophiles illustrate the ß-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.


Other References

Beilstein: 906755
UN#: UN1993
Harmonized Tariff Code:   2931.90

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-P261-P303+P361+P353-P305+P351+P338-P405-P501A

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

FlammableHarmful or Irritant

Risk & Safety

Risk Phrases: 11-36/37/38
Flammable. Irritating to eyes, respiratory system and skin.
Safety Phrases: 9-16-23-26-33-37
Keep container in a well ventilated place. Keep away from sources of ignition - No Smoking. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Take precautionary measures against static discharges. Wear suitable gloves.
Irritant Highly Flammable
TSCA: Yes