3-Chloro-1-propynyllithium

[67811-22-7] C3H2ClLi (MW 80.44) InChI = 1S/C3H2Cl.Li/c1-2-3-4;/h3H2; InChIKey = QKWLVLJHTAAJTI-UHFFFAOYSA-N (undergoes addition/substitution reactions3-5 with electrophiles; adducts with organoboranes are good sources of allenes,2 enynes,7, 8 alkenes,9 and alkynes2, 6) Alternate Name: lithium chloropropargylide. Solubility: sol ether, THF. Form Supplied in: not commercially available; used as a solution prepared prior to reaction. Preparative Method: to freshly distilled Propargyl Chloride (20 mmol) in THF (10 mL) at −70 °C is added 1.6 M Methyllithium (20 mmol) in ether. The resulting clear solution is ready for use.2 Use of n‐Butyllithium in place of MeLi is reported to result in lower yields in the subsequent reactions.3 Handling, Storage, and Precautions: highly moisture sensitive; use soon after preparation, in a fume hood.