Basic information Safety Supplier Related
ChemicalBook >  Product Catalog >  Chemical Reagents >  Organic reagents >  Silane >  Allyltrimethylsilane

Allyltrimethylsilane

Basic information Safety Supplier Related

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
  • trimethyl-2-propenyl-Silane
  • 2-(tert-butyloctasulfanyl)-2-methylpropane
  • Allyltrimethylsilane, 98+%
CAS:
762-72-1
MF:
C6H14Si
MW:
114.26
EINECS:
212-104-5
Product Categories:
  • Si-(C)4 Compounds
  • Silicon Compounds (for Synthesis)
  • Industrial/Fine Chemicals
  • Vinylsilanes, Allylsilanes
  • Si (Classes of Silicon Compounds)
  • Synthetic Organic Chemistry
  • API intermediates
Mol File:
762-72-1.mol
More
Less

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.)
Flash point:
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)
More
Less

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

More
Less

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

Synthesis

Preparation of allyl magnesium bromide Grignard reagent: Put magnesium and anhydrous ether into a 100OL reactor, heat to about 34°C, use a metering tank to pump a certain amount of 3-bromopropylene into the reactor, control the temperature at about 54°C and react for 4 hours. Preparation of allyl trimethylsilane: After the previous reaction, pump a certain amount of trimethyl chlorosilane into the reactor, control the temperature at about 54°C and react for 4 hours. Then, atmospheric distillation, and the distillate above 45°C, is the pure product.

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

Raw materials

Preparation Products

AllyltrimethylsilaneSupplier

Shanghai Guoyuan Chemical Co., Ltd. Gold
Tel
0512-55170668 13913095008
Email
shgyhg@139.com
Shanghai Qiao Chemical Science Co., Ltd Gold
Tel
021-58892003
Email
info@qiaochem.com
Nanjing Kaitian Chemical Co., Ltd Gold
Tel
133-3781-5734 15951673915
Email
2361662303@qq.com
Shanghai Ruiyi Pharmaceutical Technology Co., Ltd Gold
Tel
021-54711706
Email
sales5@ruiyitech.com
New Energy Chemicals Gold
Tel
0515-82159088 13770142076
Email
twl@njuchem.com