Propynyllithium

• CAT Number: M018350
• CAS Number: 4529-04-8
• Molecular Formula: C3H3Li
• Molecular Weight: 45.997
• Purity: ≥95%
• Synonyms: 1-PROPYNYLLITHIUM;PROPYNYLLITHIUM;Propynyllithium,90+%;1-Lithio-1-propyne;Einecs 224-862-4
• Storage: Room Temperature
• IUPAC Name: lithium;prop-1-yne
• InChI: InChI=1S/C3H3.Li/c1-3-2;/h1H3;/q-1;+1
• InChIKey: ATKCLEUSJFRRKA-UHFFFAOYSA-N
• SMILES: [Li+].CC#[C-]

Propynyllithium is an organolithium compound with the chemical formula LiC2CH3. It is a white solid that quickly decomposes upon contact with air or water. It is soluble in 1,2-dimethoxyethane, and tetrahydrofuran. To preclude degradation by oxygen and water, propynyllithium and its solutions are handled under inert gas (Ar or N2).

Reference

1: Fressigné C, Maddaluno J. Are sp lithiated carbons more nucleophilic than sp2
or sp3 ones? A comparative DFT study of the condensation of propynyllithium
aggregates on formaldehyde. J Org Chem. 2010 Mar 5;75(5):1427-36. doi:
10.1021/jo902315t. PubMed PMID: 20141113.