Tetra-n-butylammonium bromide

• Catalog No.: A10249
• CAS Number: 1643-19-2
• M. F.: C16H36BrN
• M. W.: 322.36774
• Purity: 98+%

SYNONYMS

• Title: 四正丁基溴化铵
• IUPAC name: tetrabutylazanium bromide
• IUPAC Traditional name: tetrabutylammonium bromide
• Synonyms: TBAB; Aliquat 100

DATABASE IDS

• CAS Number: 1643-19-2
• MDL Number: MFCD00011633
• EC Number: 216-699-2
• Beilstein Number: 3570983

PROPERTIES

• Purity: 98+%
• Density: 1.15
• Melting Point: 101-105°C
• GHS Hazard statements: H301-H315-H319-H335
• European Hazard Symbols: X
• GHS Precautionary statements: P261-P301+P310-P305+P351+P338-P302+P352-P405-P501A
• Risk Statements: 22-36/37/38
• Safety Statements: 26-36/37-60
• Storage Warning: Hygroscopic
• TSCA Listed: 是

REFERENCES

• 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).
• 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).
• 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).
• Phase-transfer catalyst of wide application. Some illustrative examples are given below. See also Appendix 2.
• ?-Lactones are formed by the cyclization of ?-bromoacids under phase-transfer conditions: Chem. Pharm. Bull., 29, 1063 (1981).