[3052-45-7] C₃H₅Li (MW 48.01)

InChI = 1S/C3H5.Li/c1-3-2;/h3H,1-2H2;

InChIKey = BRHWYYQFISWGOX-UHFFFAOYSA-N

(allylating agent in substitutions and additions; used to attach allyl groups to other metals and nonmetals)

Physical Data: colorless solid, pyrophoric in air.² Crystals of complex with N,N,N′,N″,N″‐Pentamethyldiethylenetriamine showed monomeric ion pairs by X-ray.³ IR,⁴ Raman,^4b UV,⁵ and ¹H,^{3, 6 13}C,⁷ and ⁷Li⁸ NMR spectra have been reported on solutions.

Solubility: sol in ethers with degrees of association 1.4–10; sparingly sol in alkanes.²

Form Supplied in: prepared in situ and used directly.

Preparative Methods: from allyl phenyl ether and Li in THF/ether is recommended for large scale, tin–lithium exchange between allyltins and phenyllithium for pure samples.⁹ Halogen–metal exchange is impractical due to fast Wurtz coupling. Allyllithium can also be made at −78 °C by the reaction of n‐Butyllithium with allyl methyl (or phenyl) selenide,¹⁰ and by metallating propene with butyllithium.¹¹

Handling, Storage, and Precautions: must be prepared and transferred under inert gas to exclude oxygen and moisture.