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 reagent in synthesis of organic compounds, especially for vinylations.[1]
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3D model (JSmol)
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3587231 | |
ChEBI |
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ChemSpider |
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ECHA InfoCard | 100.011.844 |
EC Number |
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723 | |
PubChem CID
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CompTox Dashboard (EPA)
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Properties | |
C2H3Li | |
Molar mass | 33.99 g·mol−1 |
Appearance | white solid |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards
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pyrophoric |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
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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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