Phase transfer catalyst Tetra-n-butylammonium bromide is used as a phase transfer catalyst for the preparation of lactones by cyclization of potassium salt of μ-bromocarboxylic acids and beta-lactones from beta-bromoacid by cyclization. It is also involved in the Curtius rearrangement, N-alkylation of aromatic carboxamides. It plays an important role as an ionic liquid in the regioselective O-alkylation reactions. It is also used in the preparation of polymer solar cells and single component green-light emitting electrochemical cells.
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Applications
Phase transfer catalyst Tetra-n-butylammonium bromide is used as a phase transfer catalyst for the preparation of lactones by cyclization of potassium salt of µ-bromocarboxylic acids and beta-lactones from beta-bromoacid by cyclization. It is also involved in the Curtius rearrangement, N-alkylation of aromatic carboxamides. It plays an important role as an ionic liquid in the regioselective O-alkylation reactions. It is also used in the preparation of polymer solar cells and single component green-light emitting electrochemical cells.
Solubility
Soluble in water and ethanol.
Notes
Hygroscopic. Keep the container tightly closed in a dry and well-ventilated place. Incompatible with strong oxidizing agents.
RUO – Research Use Only
General References:
- Phase-transfer catalyst of wide application. Some illustrative examples are given below. See also Appendix 2.
- K salts of ω-bromocarboxylic acids can be cyclized to lactones under effectively high-dilution conditions by extracting into toluene in the presence of a small amount of catalyst. The 16-membered ring lactone was formed in 92% yield: J. Org. Chem., 48, 1533 (1983).
- Primary alkyl chlorides can be converted to alcohols in excellent yield by phase-transfer reaction with sodium formate and hydrolysis of the resulting formate esters: Synthesis, 763 (1986).
- ß-Lactones are formed by the cyclization of ß-bromoacids under phase-transfer conditions: Chem. Pharm. Bull., 29, 1063 (1981).
- An improved procedure for the Curtius rearrangement involves reaction of acid chlorides with azide ion under phase-transfer conditions: Synthesis, 38 (1983).
- Aromatic carboxamides undergo N-alkylation with alkyl halides using KOH under solvent-free conditions: Synth. Commun., 22, 1661 (1992).
- Has been used as an ionic liquid in the regioselective O-alkylation of ambident nucleophiles: Tetrahedron Lett., 33, 4435 (1992). A method is described whereby the solvent can be recovered quantitatively. A semi-molten mixture with KF or CsF has been found to be an effective system for fluorodehalogenation of, e.g., benzyl bromide: J. Fluorine Chem., 73, 185 (1995).
- Effective catalyst for amination reactions of alkyl or activated aryl halides, by increasing the solubility of ammonia in organic media: J. Chem. Soc., Chem. Commun., 267 (1987).