311-28-4

white or tan powder

Tetrabutylammonium iodide is used in the preparation of novel quaternary amines to serve as antibacterial agents in the rise of drug-resistant bacteria,it is also used in phosphonium reversible inhibitors of cholinesterases.

Tetrabutylammonium iodide may be used as a mobile phase additive in ion-pair high-performance liquid chromatography (IP-HPLC) assay of 4-aminopyridine in serum. It may also be used as a mobile phase additive in the analysis of tetracycline by reversed-phase IPC. The addition of tetrabutylammonium iodide regulates the retention of tetracyclines.
Tetrabutylammonium iodide can be used:
As an additive in the synthesis of fused triazole derivatives using palladium catalyst.
To prepare allyl-PEG-allyl, which is a key intermediate polymer used to synthesize fluorinated amphiphilic copolymers.
As a catalyst used in the synthesis of ethers.

Tetrabutylammonium iodide (TBAI) has been used as a catalyst in the following reactions:
Synthesis of O-benzyl-N-Boc-L-tyrosine benzyl ester from N-Boc-L-tyrosine.
Conversion of 8-fluoro-1-aminonaphthalene into 1-(8-fluoro-naphthalen-1-yl)piperazine hydrochloride.
Synthesis of 1-(2,4-dichlorophenyl)-5-(4-(4-iodobut-1-ynyl)phenyl)-4-methyl-N-(piperidin-1-yl)-1H-pyrazole-3-carboxamide from 4-(4-(1-(2,4-dichlorophenyl)-4-methyl-3-(piperidin-1-ylcarbamoyl)-1H-pyrazol-5-yl)phenyl)but-3-yn-1-yl methanesulfonate.
Other reactions where TBAI can be used as a catalyst:
TBAI-tert-butyl hydroperoxide system can catalyze the conversion of α-methyl styrene derivatives into allylic sulfones by reacting with sulfonylhydrazides under metal-free conditions.
Palladium(0)-catalyzed cross-coupling between benzylic zinc bromides and aryl or alkenyl triflates.
Three-component coupling of amines, carbon dioxide, and halides to form carbamates in the presence of cesium carbonate.

Notclassified

Crystallise the iodide from toluene/pet ether (see entry for the corresponding bromide), acetone, ethyl acetate, EtOH/diethyl ether, nitromethane, aqueous EtOH or water. Dry it at room temperature under a vacuum. It has also been dissolved in MeOH/acetone (1:3, 10mL/g), filtered and allowed to stand at room temperature to evaporate to ca half its original volume. Distilled water (1mL/g) is then added, and the precipitate is filtered off and dried. It can also be dissolved in acetone, precipitated by adding ether and dried in a vacuum at 90o for 2 days. It has also been recrystallised from CH2Cl2/pet ether or hexane, or anhydrous methanol and stored in a vacuum desiccator over H2SO4. [Chau & Espenson J Am Chem Soc 108 1962 1986, Beilstein 4 IV 558.]