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Allyltrimethoxysilane

Catalog Number ACM2551839-3
CAS Number 2551-83-9
Structure
Synonyms Trimethoxyallylsilane
IUPAC Name Trimethoxy(prop-2-enyl)silane
Molecular Weight 162.26 g/mol
Molecular Formula C6H14O3Si
Canonical SMILES CO[Si](CC=C)(OC)OC
InChI InChI=1S/C6H14O3Si/c1-5-6-10(7-2,8-3)9-4/h5H,1,6H2,2-4H3
InChI Key LFRDHGNFBLIJIY-UHFFFAOYSA-N
Boiling Point 146-148
Flash Point 46°C
Purity 97%
Density 0.963 g/mL
Appearance Colorless to almost colorless clear liquid to slightly cloudy liquid
Application Allyltrimethoxysilane is a versatile allylating reagent used for the allylation of carbonyl compounds such as aldehydes, ketones, and imines. This colorless to almost colorless clear liquid plays a crucial role in the synthesis of homoallylic alcohols and amines through C-C bond formation reactions. It can also be utilized in the preparation of homoallylic α-branched amines from aromatic and aliphatic aldehyde hydrazones, and ketone hydrazones. Additionally, allyltrimethoxysilane is employed as a reagent for the introduction of double bonds onto porous silica, which is useful in the preparation of a chiral stationary phase. Its dual activation of a Lewis acid and fluoride ion enables the allylation of ketones, aldehydes, and imines. Furthermore, this reagent is crucial for regioselective generation of enol trimethoxysilyl ethers and for the synthesis of quaternary carbon centers. Notably, allyltrimethoxysilane is also involved in various reactions such as converting arylselenyl bromides to arylallylselenides and allylating aryl iodides. Its significance extends to the field of asymmetric allylation, where it serves as a key reagent in Silver-Catalyzed Asymmetric Allylation reactions.
Storage Room Temperature (Recommended in a cool and dark place, <15 °C)
Chemical Formula C6H14O3Si
Complexity 92.9
EC Number 219-855-8
Exact Mass 162.07122084
Formal Charge 0
Hazardous Materials Information This is classified as a Dangerous Good for transport and may be subject to additional shipping charges.
Heavy Atom Count 10
HS Code 2931900090
MDL Number MFCD00053865
Monoisotopic Mass 162.07122084
Reaxys Registry Number 2350745
Refractive Index 1.4036
Rotatable Bond Count 5
Specific Gravity 0.97
Topological Polar Surface Area 27.7 Ų
WGK Germany 3

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