Propargyl alcohol is a solvent stabilizer that is useful as an intermediate in organic synthesis, an electroplating brightener additive. It is useful 3-carbon fragment in acetylene coupling reactions, It undergoes Pd-catalyzed O-coupling with alcohols to give the corresponding 1-methoxyallyl ethers.
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Applications
Propargyl alcohol is a solvent stabilizer that is useful as an intermediate in organic synthesis, an electroplating brightener additive. It is useful 3-carbon fragment in acetylene coupling reactions, It undergoes Pd-catalyzed O-coupling with alcohols to give the corresponding 1-methoxyallyl ethers.
Solubility
Fully miscible in water.
Notes
Store at 4°C. Incompatible with oxidizing agent, strong acids, strong bases, amines, phosphorous pentoxide, isocyanate vapor & heat.
RUO – Research Use Only
General References:
- Yuji Kozawa; Miwako Mori. Synthesis of different ring-size heterocycles from the same propargyl alcohol derivative by ligand effect on Pd(0). Tetrahedron Letters. 2002, 43 1499-1502.
- Useful 3-carbon fragment in acetylene coupling reactions. The hydroxyl group can be protected as its THP ether; see, e.g.: Org. Synth., 76, 178 (1998), or 1-ethoxyethyl ether (see Ethyl vinyl ether, A15691): Org. Synth., 76, 199 (1998). C-Alkylation can also be accomplished without O-protection by using 2 equivalents of base (LiNH2); see, e.g., J. Chem. Soc., Perkin 1, 85 (1988); Org. Synth. Coll., 8, 415 (1993).
- O-methylation, followed by treatment with t-BuOK affords methoxyallene, a valuable reactive intermediate. It undergoes Pd-catalyzed O-coupling with alcohols to give the corresponding 1-methoxyallyl ethers: Synlett, 192 (1998). Lithiation leads to 1-lithio-1-methoxyallene: J. Org. Chem., 50, 5308 (1985); 58, 6377 (1993). For a brief feature on methoxyallene with further examples, see: Synlett, 1697 (2000).