Propynyllithium

[4529-04-8] C3H3Li (MW 46.00) InChI = 1S/C3H3.Li/c1-3-2;/h1H3; InChIKey = WRQSAQPASDQAJV-UHFFFAOYSA-N (powerful nucleophilic source of the propynyl unit for many electrophiles) Solubility: sol liquid ammonia; partially sol THF, ether. Form Supplied in: white suspension in THF; prepared in situ and used directly. Preparative Method: prepared in situ under nitrogen by reaction of propyne (condensed into cold THF) with n‐Butyllithium in THF at −78 °C2 or Lithium Amide in ether/liquid ammonia below −50 °C,3 or by reaction of 1,2-dibromopropane with 3 equiv of Lithium Diisopropylamide (double elimination of hydrogen bromide and deprotonation) at −60 °C to 0 °C in THF.4 Handling, Storage, and Precautions: must be prepared and transferred under inert gas (Ar or N2) to exclude oxygen and moisture.