| |
| Identifiers | |
|---|---|
3D model (JSmol) |
|
| 3587231 | |
| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.011.844 
|
| EC Number |
|
| 723 | |
PubChem CID |
|
CompTox Dashboard (EPA) |
|
| |
| |
| Properties | |
| C2H3Li | |
| Molar mass | 33.99 g·mol−1 |
| Appearance | white solid |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards |
pyrophoric |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
Vinyllithium is an organolithium compound with the formula LiC2H3. A colorless or white solid, it is encountered mainly as a solution in tetrahydrofuran (THF). It is a reagentinsynthesis of organic compounds, especially for vinylations.[1]
Solutions of vinyllithium are prepared by lithium-halogen exchange reactions. A halide-free route entails reaction of tetravinyltin with butyllithium:
The reaction of ethylene and lithium affords vinyl lithium and lithium hydride, together with other organolithium compounds,[1]
Like most organolithium compounds, vinyllithium crystallizes from THF as a cluster compound as a cubane-type cluster.[2]
Vinyllithium is used to install vinyl groups on metal-based reagents, i.e., vinylations. It is a precursor to vinylsilanes, vinylcuprates, and vinylstannanes.[3] It adds to ketones compounds to give allylic alcohols. Vinylmagnesium bromide is often used in place of vinyllithium.[4]
Vinyl magnesium bromide, a Grignard reagent, is in many ways easier to generate in the laboratory and behaves similarly to vinyllithium.[5]
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