ChemicalBook > Product Catalog > Chemical Reagents > Organic reagents > Silane > Allyltrimethylsilane
Allyltrimethylsilane Chemical Properties
- Boiling point:84-88 °C (lit.)
- Density 0.719 g/mL at 25 °C (lit.)
- refractive index n
- Flash point:45 °F
- storage temp. 2-8°C
- solubility freely sol all organic solvents.
- form Liquid
- color Clear colorless
- Specific Gravity0.72
- Water Solubility insoluble
- Hydrolytic Sensitivity2: reacts with aqueous acid
- BRN 906755
- CAS DataBase Reference762-72-1(CAS DataBase Reference)
- NIST Chemistry ReferenceSilane, trimethyl-2-propenyl-(762-72-1)
- EPA Substance Registry SystemSilane, trimethyl-2-propenyl- (762-72-1)
Allyltrimethylsilane Usage And Synthesis
- Chemical Propertiesclear colourless liquid
- Physical propertiesbp 85–86°C, d 0.717 g cm?3.
- UsesAs 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.
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.
- Purification MethodsFractionate 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
- Raw materialsChlorotrimethylsilaneAllyl bromide
- Preparation Products4-(1-BENZYLPIPERIDIN-4-YLOXY)-3,5-DICHLOROBENZENAMINE
- POTASSIUM ALLYLTRIFLUOROBORATE ALLYLTRIS(TRIMETHYLSILOXY)SILANE VINYLOXYTRIMETHYLSILANE Triethylvinylsilane ALLYLTRIMETHOXYSILANE Allyltributyltin Allyl methyl sulfide ALLYLOXYTRIMETHYLSILANE ALLYLOXY-T-BUTYLDIMETHYLSILANE allyltrimethylammonium chloride Allyltriphenylphosphonium bromide 3-Allyloxy-2-Hydroxy-1-Propane,Sodium Salt ALLYLMAGNESIUM BROMIDE 2-(Trimethylsilylmethyl)allyl acetate ALLYLTRIISOPROPYLSILANE 2,3,5,5-TETRAKIS(TRIMETHYLSILYL)-1,3-CYCLOPENTADIENE 3-(TRIMETHYLSILYL)CYCLOPENTENE 2-CHLOROMETHYL-3-TRIMETHYLSILYL-1-PROPENE
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