Allyltrimethylsilane

Allyltrimethylsilane Basic information
Product Name:Allyltrimethylsilane
Synonyms:Allyltrimethylisilane;trimethyl-prop-2-enyl-silane;Allyltrimethylsilane(3-trimethylsilyl-1-propene)99%available;Silane,trimethyl-2-propenyl-;trimethyl-2-propenyl-silan;Allyltrimethylsilane, 98+%;Allyltrimethylsilane,99%;Allyltrimethylsilane,97%
CAS:762-72-1
MF:C6H14Si
MW:114.26
EINECS:212-104-5
Product Categories:Si-(C)4 Compounds;Silicon Compounds (for Synthesis);Vinylsilanes, Allylsilanes;Si (Classes of Silicon Compounds);Synthetic Organic Chemistry;Industrial/Fine Chemicals;API intermediates
Mol File:762-72-1.mol
Allyltrimethylsilane Structure
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 Gravity0.72
color Clear colorless
Water Solubility insoluble
Hydrolytic Sensitivity2: reacts with aqueous acid
BRN 906755
Stability:Volatile
InChIKeyHYWCXWRMUZYRPH-UHFFFAOYSA-N
LogP4.64 at 20℃
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)
Safety Information
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
MSDS Information
ProviderLanguage
Allyltrimethylsilane English
SigmaAldrich English
ACROS English
ALFA English
Allyltrimethylsilane Usage And Synthesis
Chemical Propertiesclear colourless liquid
UsesAllyltrimethylsilane 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.
PreparationAllyltrimethylsilane is synthesized by the reaction of trimethylchlorosilane and allylmagnesium bromide.
ApplicationAllyltrimethylsilane is used in the allylation of aldehydes, imines, allylic and benzylic alcohols, and chiral α-keto-amides that are derived from (S)-proline esters.
ReactionsAllyltrimethylsilane 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).
Allyltrimethylsilane Reactions
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 ExplosibilityFlammable
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.]
POTASSIUM ALLYLTRIFLUOROBORATE DIALLYLDIPHENYLSILANE TRIMETHYLSILANE (Trifluoromethyl)trimethylsilane ALLYL(CHLOROMETHYL)DIMETHYLSILANE 2,3,5,5-TETRAKIS(TRIMETHYLSILYL)-1,3-CYCLOPENTADIENE ALLYLTRIISOPROPYLSILANE (2,4-PENTADIENYL)TRIMETHYLSILANEDISC 06/13/03 DIALLYLDIMETHYLSILANE TRIMETHYLSILYLMETHYLALLENE METHYLSILANE 3,3-DIMETHYLALLYLTRIMETHYLSILANE ETHYL 2-(TRIMETHYLSILYLMETHYL)ACRYLATE 2-CHLOROMETHYL-3-TRIMETHYLSILYL-1-PROPENE (2-BROMOALLYL)TRIMETHYLSILANE (1-HYDROXYALLYL)TRIMETHYLSILANE (2-METHYL-PROPENYL)TRIMETHYLSILANE 3-(TRIMETHYLSILYL)CYCLOPENTENE

Email:[email protected] [email protected]
Copyright © 2024 Mywellwork.com All rights reserved.