| 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 |
