(2-Bromoallyl)Trimethylsilane

• CAS: 81790-10-5
• Catalog Number: ACM81790105
• Category: Other Products
• Molecular Weight: 193.16 g/mol
• Molecular Formula: C6H13BrSi
• IUPAC Name: 2-bromoprop-2-enyl(trimethyl)silane
• Canonical SMILES: C[Si](C)(C)CC(=C)Br
• InChI: InChI=1S/C6H13BrSi/c1-6(7)5-8(2,3)4/h1,5H2,2-4H3
• InChI Key: LUPQCAARZVEFMT-UHFFFAOYSA-N
• Flash Point: 30 °C
• Appearance: Colorless to Light orange to Yellow clear liquid
• Application: (2-Bromoallyl)Trimethylsilane is designed to serve as a versatile synthon in organic synthesis. It can be transformed into valuable intermediates like CH2=CHCH2TMS and CH2=CBrCH2- for the creation of 1-trimethylsilylmethyl-substituted 1,3-butadienes. From this compound, the 1-trimethylsilylmethylvinyl anion is easily prepared, enabling the incorporation of this group into various substrates. This includes facilitating reactions such as the ring opening of 1-butene oxide with a Grignard reagent in the presence of copper(I) iodide, leading to a regioselective product. Moreover, subsequent transformations like desilylative oxidation produce α-methylene-γ-lactones, showcasing the synthon's utility as a 1-hydroxymethylvinyl anion equivalent. It also offers an avenue to generate unstable β,γ-unsaturated lactones from trans-2,3-epoxybutane. Additionally, the compound's allylsilane component can promote smooth copper-catalyzed 1,4-additions to otherwise non-reactive substrates, as well as high-yield ethylaluminum dichloride-induced cyclizations, illustrating its broad synthetic applications.
• Storage: <0 °CStore under inert gas
• Complexity: 91.2
• Covalently-Bonded Unit Count: 1
• Exact Mass: 191.99699g/mol
• Formal Charge: 0
• Hazard Statements: H315 : Causes skin irritation.; H319 : Causes serious eye irritation.; H226 : Flammable liquid and vapour.
• H-Bond Acceptor: 0
• H-Bond Donor: 0
• Heavy Atom Count: 8
• MDL Number: MFCD00043054
• Monoisotopic Mass: 191.99699g/mol
• Precautionary Statements: P210 : Keep away from heat, hot surfaces, sparks, open flames and other ignition sources. No smoking.; P264 : Wash skin thoroughly after handling.; P280 : Wear protective gloves/ protective clothing/ eye protection/ face protection.; P370 + P378 : In case of fire: Use dry sand, dry chemical or alcohol-resistant foam to extinguish.; P337 + P313 : If eye irritation persists: Get medical advice/ attention.; P303 + P361 + P353 : IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water.
• PubChem ID: 87564596
• Rotatable Bond Count: 2
• Signal Word: Warning
• Specific Gravity: 1.13