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| | Allyltrimethylsilane Basic information |
| | Allyltrimethylsilane Chemical Properties |
| Boiling point | 84-88 °C (lit.) | | density | 0.719 g/mL at 25 °C (lit.) | | vapor pressure | 82hPa at 25℃ | | refractive index | n20/D 1.407(lit.) | | Fp | 45 °F | | storage temp. | 2-8°C | | solubility | freely sol all organic solvents. | | form | Liquid | | Specific Gravity | 0.72 | | color | Clear colorless | | Water Solubility | insoluble | | Hydrolytic Sensitivity | 2: reacts with aqueous acid | | BRN | 906755 | | Stability: | Volatile | | InChIKey | HYWCXWRMUZYRPH-UHFFFAOYSA-N | | LogP | 4.64 at 20℃ | | CAS DataBase Reference | 762-72-1(CAS DataBase Reference) | | NIST Chemistry Reference | Silane, trimethyl-2-propenyl-(762-72-1) | | EPA Substance Registry System | Silane, trimethyl-2-propenyl- (762-72-1) |
| Hazard Codes | F,Xi | | Risk Statements | 11-36/37/38 | | Safety Statements | 16-26-36-23-33-7/9 | | RIDADR | UN 1993 3/PG 2 | | WGK Germany | 3 | | TSCA | Yes | | HazardClass | 3 | | PackingGroup | II | | HS Code | 29310095 |
| | Allyltrimethylsilane Usage And Synthesis |
| Chemical Properties | clear colourless liquid | | Uses | Allyltrimethylsilane is a general reagent to introduce allyl groups across acid chlorides, aldehydes, ketones, iminium ions, enones, and for cross-coupling with other carbon electrophiles. It is used as a reagent in Hosomi?Sakurai reaction. | | Preparation | Allyltrimethylsilane is synthesized by the reaction of trimethylchlorosilane and allylmagnesium bromide. | | Application | Allyltrimethylsilane is used in the allylation of aldehydes, imines, allylic and benzylic alcohols, and chiral α-keto-amides that are derived from (S)-proline esters. | | Reactions | Allyltrimethylsilane is involved as a reactant in Hosomi Sakurai reaction for allylation in the presence of Lewis acid. For example, it reacts with cyclohexanone to get 1-allylcyclohexanol. It acts as a nucleophile and is involved in Carbon-Ferrier rearrangement.
As a Carbon Nucleophile in Lewis Acid-Catalyzed Reactions.
Allyltrimethylsilane is an alkene some 10 times more nucleophilic than propene, as judged by its reactions with diarylmethyl cations.It reacts with a variety of cationic carbon electrophiles, usually prepared by coordination of a Lewis acid to a functional group, but also by chemical or electrochemical oxidation,or by irradiation in the presence of 9,10- dicyanoanthracene.
carbon to give an intermediate cation, and the silyl group is lost to create a double bond at the other terminus. Among the more straightforward electrophiles are acid chlorides (eq 1).
As a Carbon Nucleophile in Fluoride Ion-Catalyzed Reactions.
The reactions with aldehydes, ketones (eq 23),54 and α,β-unsaturated esters (eq 24)55 can also be catalyzed by fluoride ion, usually introduced as tetra-n-butylammonium fluoride (TBAF), or other silicophilic ions such as alkoxide. These reactions produce silyl ether intermediates, which are usually hydrolyzed before workup. The stereochemistry of attack on chiral ketones can sometimes be different for the Lewis acid- and fluoride ion-catalyzed reactions.
Other Reactions.
Allyltrimethylsilane reacts with some highly electrophilic alkenes, carbonyl compounds, azo compounds, and singlet oxygen to a greater or lesser extent in ene reactions that do not involve the loss of the silyl group, and hence give vinylsilanes in a solvent-dependent reaction. | | Flammability and Explosibility | Flammable | | Purification Methods | Fractionate it through an efficient column at atmospheric pressure. If impure, dissolve it in THF, shake it with H2O (2x), dry (Na2SO4), filter and fractionate it. [Cudlin & Chvalovsky′ Collect Czech Chem Commun 27 1658 1962, Beilstein 4 IV 3927.] |
| | Allyltrimethylsilane Preparation Products And Raw materials |
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